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15 Best Tours in Chicago (by a Local)

The Windy City is the third largest city in the United States and comes with a variety of delights for any visitor. From food and craft beer to architecture and history, the Midwestern metropolis is packed with exciting experiences.

There are a variety of great tours run by locals across the city that help you dive deep into the things that matter most to Chicagoans. The unique history and culture of the city is best discovered with a local guide, and these tours will help you to dive deeper into what makes the city tick.

I’m a Chicago local and have been on many tours with friends and family visiting. To get you started here’s my list of the best tours in Chicago.

1. Chicago Skydeck + “The Ledge” Experience Ticket

The Willis Tower is the tallest Skyscraper in Chicago and this ticket allows you to go to the very top.

There are a bunch of exhibits on the way, to teach you about Chicago’s history and the deep cultural roots that connect the city. Once at the top, brave visitors can step into ‘the Ledge,’ a series of four glass balconies that give you views across Chicago as well as over the street below.

A theatrical presentation is also included in the ticket, which discusses the construction of the Willis Tower.

2. Chicago River Architecture Cruise

For a more relaxing tour experience, this river cruise takes you down the Chicago River whilst also discovering the architecture of the city and the history behind some of the most iconic buildings.

The 75-minute-long tour passes more than 40 different monuments, as well as a variety of the city’s most well-known bridges.

The commentary is provided by a live guide on board the ship, and there is a bar available for you to purchase refreshments and drinks. This is actually one of the tours I personally like most for first-time visitors. You can also check out my guide on the best boat tours in Chicago .

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3. Wicker Park Walking Food Tour

Like many cities across the United States, Chicago is well known for its growing food culture and Wicker Park is a hub for the culinary scene in the city. This three-hour tour is conducted by a local with extensive knowledge of the best food to try in the city.

You will sample typical Chicagoan food from five different restaurants in the area, all offering their own little slice of the city. This is a great dinnertime tour that will provide you with more than enough food to make a full meal, so come with a full appetite.

4. 90-Minute Mob and Crime Bus Tour

Discover the dark underbelly of Chicago from the safety of a tour bus with this tour, which tackles the history of mobsters and criminals in the city.

You will learn about Al Capone, John Dillinger and many other famous criminals from the city in this tour which lasts around 90 minutes.

You will be shown the different sites that have been influenced by crime in the city, and be able to follow in the footsteps of the most notorious mobsters. You can also delve deeper into the history of the subject at the small mobster museum located in the city.

5. Treasures of Chicago’s Golden Age: 90-Minute Walking Tour

The city experienced a major boom in the late 19th century, which extended right through to the early years of the following century.

This tour takes you around all of the architectural highlights from the era when the city was in major expansion and people were flocking from across the United States to the Windy City. Your skilled local guide will discuss the different factors that influenced Chicago’s expansion, as well as highlight the important historical events that still shape the city to this day.

This tour focuses on the people that built Chicago, giving it a nice personal touch. I highly recommend taking a walking tour on the first day of your visit, it offers plenty of tips on what to do the coming days as well.

6. Chicago Secret Food Tour

Chicago is full of famous restaurants and bars, however this tour aims to take you to the best restaurants that are not well-known by visitors.

You will visit six different spots around the Loop District of Chicago, and learn about the important influence Italian immigrants had on the city. The walking tour takes around three hours to complete, and is paced so you can truly savor all of the dishes you are sampling.

Some drinks are also included. The tour also discusses the local art and architecture in the area, making it a great tour for your first evening in the city.

7. Loop Interior Architecture: 2-Hour Walking Tour

This tour takes you inside the most famous buildings to talk about how the magnificent architecture has been taken indoors.

You will get an extensive tour of the entrances and corridors of these buildings from a knowledgeable local guide, who will discuss the history found within their walls and the lives of the architects who designed them.

You will also be able to check out the underground Pedway System, which has shaped how the rest of the city was designed and changed the lives of locals for decades.

Related reading :  Best Things to Do in Downtown Chicago

8. Chicago Hop-on-Hop-off Bus Tour: Classic, Premium or Deluxe

Hop-on-hop-off bus tours are a great way to become acquainted with a new city and gather your bearings. This tour takes you to all of the main sights in the city for you to explore at your own pace.

Audio guides are included to give you more information, and these are available in multiple languages. You can customise your ticket to last either one or two days, and to also include a night bus option. Free WiFi is available on all of the buses, and all guests are given a free bag of Garrett’s Popcorn to snack on whilst enjoying the tour.

I recommend it as a great way to get around the city during your entire visit (there’s 24, 48 and 72 hour option).

9. Gourmet Brunch, Lunch, or Dinner River Cruise

Delight your taste buds with a scrumptious meal prepared by talented chefs, offering a variety of brunch, lunch, or dinner options. Knowledgeable guides provide captivating commentary on the city’s history and architectural wonders, showcasing landmarks like Willis Tower and Navy Pier.

This unique blend of exquisite cuisine, breathtaking scenery, and informative narration promises an unforgettable journey through Chicago’s heart.

Read next :  15 Best Day Trips from Chicago

10. Chicago’s Modern Skyscrapers Guided Walking Tour

Chicago has some of the highest skyscrapers in the city. If one of your main aims for your trip is to check them out, then this walking tour can help you take in the most famous buildings in Chicago.

The local guide will help you understand the history behind all of the skyscrapers, as well as talk at length about the innovations made by architects in the city.

You will learn more about the modernist movement that shaped the city’s skyline and still influences new buildings to this day.

11. Private Helicopter Flight

For the ultimate nighttime tour of the city, this helicopter experience is a fantastic option if you are looking to splurge.

The pilot is fully licensed and experienced, and comes from the local area so is able to provide high-quality commentary about all of the sights you can see from the sky.

From skyscrapers, to the wild waves of Lake Michigan, you can truly see it all from this helicopter experience. All safety equipment is provided and customers are given a short briefing before take-off. Might be an obvious tip but I recommend this experience during a clear day.

12. Navy Pier Centennial Wheel

The Chicago Navy Pier Centennial Wheel offers an exciting experience at one of the city’s most iconic landmarks. With this tour, visitors can enjoy stunning views of Chicago’s skyline and Lake Michigan from the impressive Centennial Wheel. The tour provides various ticket options, allowing guests to customize their experience.

Whether opting for a standard ride, a fast pass, or a private gondola, I highly recommend it to take in breathtaking panoramic view of the city.

Related :  15 Best Hotels in Chicago

13. Bobby’s Bike Hike Chicago: Lakefront Neighborhoods Tour

Featuring some of the wealthiest districts in Chicago, the Lakefront Neighborhoods Tour can provide a relaxed and fulfilling experience during your stay in Chicago.

This tour is done on bikes, helping you to enjoy a more active adventure as well as explore the neighbourhoods at an easy pace. You will be able to check out the local mansions, as well as the Lincoln Park Zoo.

The Lakeside area, where the tour ends, is also a good spot for photo opportunities. This tour accepts all ages, making it a good option for families.

14. Chicago South Side Tour with Optional River Cruise

For visitors more interested in the history of the city, the South Side region is definitely worth a visit.

In this tour, a local guide will talk to you about the founding of the city, and the important landmarks in the South Side region that display the complex and vibrant history of Chicago.

You will also be taken to Jackson Park to enjoy some recreational activities, and to the Art Institute to see the world’s largest collection of Impressionist Art.

This two-hour tour finishes up at the University of Chicago, where you can enjoy the ornate English architecture.

15. Chicago Haunted Bar Tour

Most major American cities have their ghost stories, and Chicago is no exception. Learn all about the macabre past of Chicago and hear captivating ghost stories along the way.

This tour takes you to four different bars across the city, where you can spend some time soaking up the atmosphere and enjoying a local beverage. The tour lasts around two and a half hours, and is great if you are looking for a unique night out in the city.

15 Best Tours in Chicago (by a Local):

• Chicago Skydeck + “The Ledge” Experience Ticket
• Chicago River Architecture Cruise
• Wicker Park Walking Food Tour
• 90-Minute Mob and Crime Bus Tour
• Treasures of Chicago’s Golden Age: 90-Minute Walking Tour
• Chicago Secret Food Tour
• Loop Interior Architecture: 2-Hour Walking Tour
• Chicago Hop-on-Hop-off Bus Tour: Classic, Premium or Deluxe
• Gourmet Brunch, Lunch, or Dinner River Cruise
• Chicago’s Modern Skyscrapers Guided Walking Tour
• Private Helicopter Flight
• Navy Pier Centennial Wheel
• Bobby’s Bike Hike Chicago: Lakefront Neighborhoods Tour
• Chicago South Side Tour with Optional River Cruise
• Chicago Haunted Bar Tour

The Top 23 Excursions and Tours in Chicago

If you’re planning some sightseeing in the Windy City, there are so many excursions to choose from. Try these top tours in Chicago!

Chicago, Illinois is famous for its amazing deep-dish pizza, beautiful architecture,  gorgeous waterfront, and unique history. It’s also one of the top tourist destinations in the Midwest and it’s no surprise why!  The city has a ton to offer visitors whether you’re interested in culture, sports, outdoor activities, or nightlife.  

We know that it can be a bit confusing to know where to even start when you’re planning a visit to a city with so many options so to help you get started, we have created this list of the top tours and activities to do in the Windy City.

So Many Ways to See Chicago

If you’re planning a trip to the Windy City, you can’t go wrong with scavenger hunt tours by Let’s Roam ! These walking tours in Chicago are app-guided , and there are options to suit any traveler. From family-friendly sightseeing experiences to adult-oriented pub crawls , there’s no shortage of fun!

The Best Excursions and Tours in Chicago

Below you’ll find a list of the best tours and excursions to do in Chicago.  This is based on the experience of our own in-house travel experts as well as TripAdvisor and Google Map reviews.  Some of them are walking tours while others rely on buses to get around. There are also a few that are adults-only so you may want to skip on those if you’re traveling with the kiddos!

Disclosure: All of the tour departure times and locations were correct at the time of writing however, it’s important to double-check the information before heading out for the tour as these may change, especially if COVID restrictions are put back in place.

Chicago Walking Tours

With its grid-like streets and lovely Riverwalk, Chicago is a fabulous place for walking. Combine this with the show-stopping architecture and the engrossing history and you have all the ingredients that you need for days spent exploring the streets.  While it’s great to stroll along on your own, a sightseeing tour of the city will let you see a whole different side of a city and help you learn the finer details of what makes the city tick. It’s great to do one at the start of your visit as your tour guides can give you great insight into some of the best places to go for dinner or drinks after the tour and if you’re traveling on a budget, you may learn some great money-making tips!

1. Riverwalk & North Loop Tour

Run by Free Chicago Walking Tours , this two-hour walking tour gives an in-depth look into the history of Chicago going all the way back to the late 17th-century until today. The tour covers everything from the role that Chicago played in the Revolutionary War to the Roaring 20s and as you stroll through the Loop, you’ll see the Chicago River, Daley Plaza, the Chicago Cultural Center, and more.  The tour is on a pay-as-you-wish basis so you can be sure that the guides will work hard for their money! 

2. Let’s Roam Chicago Sightseeing Scavenger Hunts

Here at Let’s Roam, we think one of the best ways to get to know a city is through a destination scavenger hunt! On this intriguing   Chicago Loop hunt , you’ll be asked fun trivia questions about some of Chicago’s top attractions including The Bean, the Art Institute of Chicago, the Crown Fountain, and the world-famous Tiffany Dome. You’ll also have plenty of prompts to take great photos to remember your trip by! You’ll learn a lot about Chicago’s storied buildings and epic sculptures!

Once you have finished up with the Loop hunt, don’t forget to go back and do the Magnificent Mile Scavenger Hunt to see sites like Washington Square Park, the Tribune Tower, and the Wrigley Building.  Both tours take around an hour and can be conveniently done on your smartphone using the Let’s Roam app.

3. Chicago Gangsters and Ghosts Tour

After seeing Chicago’s famous attractions, it’s time to go into its underbelly and learn about the gangsters that used to rule this joint.  Chicago is infamous for its gangster past and during the 1920s and 1930s, mobsters were in control of much of the city.  100 years ago, murder and mayhem lurked in the shadows, and today, you can hear all about the men (and women!) that left their mark on Chicago.  

This fascinating (and occasionally bone-chilling Chicago Gangsters and Ghosts Tour is a two-hour-long affair that takes you through the Chicago Loop Vice District, stopping by the Congress Hotel, Death Alley, the Palmer House, and many other creepy places.  Rather than being a theatrical display, the guides tell the stories in a somber, delicate way that makes it easy to understand the impact that the mobs had on the psyche of the city.  Tours leave throughout the day with three daytime tours and one evening tour and you can book tickets online.

4. Dazzling Interiors of the Loop

Chicago is well known for its interesting blend of architectural styles and people around the world can easily identify its skyline. However, few people get a chance to see some of Chicago’s most striking Interiors and Inside Chicago’s Walking Tours wants to change this with their two-hour-long Dazzling Interiors Tour.  During the tour, you’ll get a chance to see the remarkable interiors hidden behind some of Chicago’s most famous facades.  Some of the highlights of the tour are art-deco lobbies, gilded ceilings, and early designs by master architect Frank Lloyd Wright. Tours cover just one and a half miles so they are suitable for people of all ages and this is the perfect way for art lovers to get an in-depth look at some of Chicago’s most distinctive buildings. 

5. Off the Grid Tour

Offered by Free Chicago Walking Tours , a pay-as-you-wish tour operator, the Off the Grid Tour veers off the standard tourist route and visits some of the city’s most Instagrammable spots including Death Alley, the Chicago Cultural Center, and the Pink Flamingo Wall at Flamingo Rum Club.  The tour starts at the ACME Hotel in the River North before leading you through the Loop where you can get photos in front of Chicago’s most recognizable landmarks before finishing up the world’s largest Tiffany Glass Dome.  

The Off the Grid tours are only held sporadically throughout the year so if you aren’t able to join one—don’t worry!  There are still plenty of other free walking tours to choose from including the Loop Interior Tour, the Crime & Gangster Tour, the Millenium Park Tour, and many more.  Take a look at their website for more information. 

Bike and Segway Tours

Walking is one of our favorite ways to explore a new destination but, sometimes, having your own set of wheels. Bike and segway sightseeing tours let you explore a city at a quick pace while staying having the time to soak up the atmosphere.  

6. Bikes, Bites & Brews Tour

What better combination can there be than biking, beer, and bite-sized treats.  During this four-hour tour led by Bobby’s Bike Hike Chicago , riders will cover a whopping 13 miles across Gold Coast, Lakeview, Lincoln Park, and Wrigleyville, making perfectly timed pit stops along the way where they can give their taste buds a workout with pizza, hot dogs, cupcakes, and, of course, beer.  

The wonderful guides and the long route make this the perfect introduction to the city and lets visitors cover an impressive amount of ground in a short period of time. The cost of the tour includes bike rental, food, and drinks and riders must be at least 21 years old.  If you would like to go on a family-friendly version of the tour, they also offer Bobby’s Bike Hike Chicago’s Family Food & Bike Tour. If you love biking, this is one tour of Chicago that you won’t want to miss!

7. Chicago Lakefront Segway Tour

With its relatively flat terrain and sweeping lakefront, Chicago is a fantastic city to explore by segway. Absolutely Chicago Segway Tours gives travelers the opportunity to zoom by some of the city’s most iconic attractions including Millennium Park, Monroe Harbor, and Museum Campus, home to the Shedd Aquarium, Soldier Field, the Field Museum, and much, much more on this eight-mile-long adventure.  Tours last roughly two to two and a half hours and the insightful and entertaining tour guides along with the thrill of riding a segway will make the time go by in a blink of an eye. Absolutely Chicago has a wide range of tours covering different areas of the city as well as themed tours like the Chicago Mob and Gangster Tour and a chilling ghost tour.

While we love the idea of going on walking tours, sometimes the weather (or our bodies!) just isn’t cooperating with us and it’s time to join one of Chicago’s many bus tours.  If you’re tight on time, bus tours are a great way to see many different areas of the city or if you have a bit more time to spare, they are a great way to discover the neighborhoods that you want to go back to!

8. Hop-On Hop-Off Bus Tour

It can be a bit challenging to plan a trip full of exciting sightseeing adventures (trust us, we know!) but Big Bus makes it easy to get a great overview of Chicago without even having to leave the comfort of your bus seat (but it’s much better if you do!).  These useful bus tours allow passengers to get on and off as often as they wish at one of the conveniently located stops.  This allows you to see the things that you want but skip the things that you aren’t interested in. Most tour packages are good for one day (roughly eight hours) and it’s possible to “upgrade” your ticket to include extra activities or even extra days.  Expert tip: Keep a close eye out for the bus signs or make a mental note of where you got off the bus as they can be really hard to see at a few of the attractions. 

9. See It All Minibus Tours 

If you love the idea of a bus tour but aren’t sure that the hop-on-hop-off buses are right for you, you may want to consider one of the See It All Minibus Tours .  During the tour, you’ll be whisked around downtown and the north side of the city in a climate-controlled minibus, passing by the Loop, Millennium Park, the Buckingham Fountain, the Wrigley Building, the Chicago River, Lincoln Park, and even the Original Playboy Mansion. 

There is an entertaining narration that plays throughout the journey telling you about the city’s long history and colorful characters and you can hop out and take photos at four designated photo stops along the way. 

If you want to keep the fun going after the tour, you can add on a Chicago River Architecture Boat Tour.

10. Family Secrets Bus Tour

If you want to get an inside look at a modern-day Soprano-like organized crime family, this unique tour can take you deep into the world of the mafia. The Family Secrets tou r is run by Frank Calabrese Jr. who once worked as a soldier in his dad’s Chinatown crew.  During the two-hour bus tour, he gives an unfiltered, firsthand account of life in the mob by telling stories of the drama and endless killings that he witnessed.  He takes you to actual crime scenes in the areas where the Chicago Mob once worked, lived, and played.   Private tours are available throughout the week and begin outside of the Chicago Chop House on West Ontario Street. 

11. Chicago Crime and Mob Bus Tour

Organized by Chicago Crime Tours and Experiences , this crime-themed two-hour-long bus tour gives visitors the chance to go deep into the world of Al Capone, John Dillinger, and The Untouchables, who ultimately brought them down through a series of stops at well-known crime sites, including the site of the infamous Valentine’s Day Massacre, and the courthouses where the city’s most prolific criminals had to stand trial for their crimes.  While their signature tour is offered during the day, there is also a two-and-a-half-hour-long nighttime tour that puts everything in an even darker light!

Food Tours and Bar Crawls

Here at Let’s Roam, two of our favorite pastimes include eating and touring so food tours are one of our must-do activities wherever we go. Food tours are an amazing way to not only try some hidden culinary gems but they are also perfect for learning more about some of the off the beaten track parts of a city. 

12. Gateway to the West Loop Food Tour

With a slew of mouth-watering delights hidden in eateries all across the city, it can be tough to know where to go for the best eats in the Windy City. Chicago Food Planet’ s three-hour-long Gateway to the West Loop Food Tour helps you get your hands on some of the best dishes that the city has to offer ranging from pizza to doughnuts.  Throughout the tour, you’ll learn insider information about the history of both Chicago and the West Loop and your guides will be more than happy to impart some local wisdom.  Make sure to come hungry as they give out some hefty portions during this tour. 

If you’re blown away by this tour, they also have a food tour of Chinatown.

13. Original Chicago Pizza Tour

If there is one food that you absolutely must try in Chicago, it has to be the deep dish pizza. On this tour led by Chicago Pizza Tours , you’ll get to visit some of the city’s most beloved, independently-owned pizzerias.  The tour includes six or more slices of pizza (wow!) and the guides are informative and fun and will teach you about a lot more than just pizza which makes it well worth the money.  They offer bus tours and walking tours so it’s perfect for people with mobility issues and if you want to make it a bit more festive, you can opt for the Chicago Pizza and Cocktail Tour. 

14. Taste of Chicago Food Tour

This is another food tour that’s sure to please even the pickiest of eaters. Run by Tastebud Tours , this appetite extravaganza takes you through Chicago’s downtown Loop stopping at many of the area’s most popular eateries to try the deep-dish pizza, sandwiches, and desserts. The tour guides will point out some of downtown’s most important attractions on the way and will impress you with this encyclopedic knowledge and endless enthusiasm.  

15. Historic Chicago Walking Bar Tour

History lovers who want to learn more about the Prohibition era can join this part-history tour, part-bar crawl offered by the team at Chicago Detours .  During the two-and-a-half-hour tour, you’ll visit some of Chicago’s most historic bars and pubs including a Jazz Age Hotel and the  Billy Goat Tavern, located inside a 19th-century mansion.  

If you’re looking for another off-beat tour, Chicago Detours also runs an 1893 World’s Fair Tour and a Chicago Neighborhoods Tour that takes you into the north, west, and south sides of the city and includes a stop in a neighborhood dive bar and the opportunity to dine at a home-style Polish restaurant. Yum!

16. Chicago Prohibition Bus Tour 

This bus tour is certainly unique!  The three-and-a-half-hour Chicago Prohibition Bus Tour visits four former speakeasies where you can learn about this eventful period in Chicago’s history including the types of drinks that people would have ordered when they strutted up to the bar.  All of the stops on the tour are very different so you don’t need to worry about things feeling repetitive and the smooth-talking guides help move the evening along nicely.  If you want to get some exercise, there is also a walking version that lasts two and a half hours.

17. Chi-town Bar Crawl Scavenger Hunt

If you want a unique take on the standard bar crawl, the Let’s Roam’s Chi-town Bar Crawl may be right up your alley! Here, you can battle your closest friends and drinking buddies to crazy challenges until one of you is the champion of Chi-town. The challenges go from easy-peasy to difficult and are perfectly designed to bring out your competitive side and you may even discover a new favorite hangout or rediscover your old stomping grounds. While the hunt normally takes around one and a half to two hours, you can make it as long or as slow as you want!

Between the enormous and sparkling Lake Michigan to the quaint and charming Chicago River, Chicago is a watery city so it probably comes as no surprise that one of the best ways to explore is by boat! Luckily, there is a huge array of sightseeing cruises to choose from and virtually all of them will give you great views.  Just keep in mind that Chicago has earned the nickname the Windy City for a reason and umbrellas may not be the best things to use as rain cover if you’re going on a boat tour. It is a good idea to pack a waterproof jacket or a poncho with you just in case!

18. Chicago Architecture Foundation River Cruise

This special architecture cruise takes visitors along the Chicago River while expert volunteer docents tell them the inside scoop on 50 of Chicago’s most notable buildings.  The Chicago Architecture Foundation’s River Cruise uses the fleet of Chicago’s First Lady Cruises for these 90-minute tours which means that you’re in the hands of professional staff and have access to full-service bars and open-air upper decks that are the perfect spot to get some great photos.  There are daytime and nighttime sailings and, for just about $5 more, you can also visit the Chicago Architecture Center.  

19. Chicago Sunset Cruise

This relaxing cruise run by Wendella Tours and Cruises is one of the best ways to finish off a long day of sightseeing.  During the 90-minute cruise on Lake Michigan, you’ll watch as the sun sets behind the city skyline and turns the sky into a swirl of pink, orange, and red.  The cruises have a full bar where you can purchase drinks and snacks and there is a climate-controlled lounge area that keeps you warm in the winter and cool in the summer.  The cruises leave from Michigan Avenue. The departure times vary throughout the year so make sure to check their website for the most up-to-date information and to book tickets.  

If you want something a bit shorter or only have time during the day, they also offer a 45-minute architecture tour on the Chicago River.  This tour will highlight some of the most famous Chicago landmarks and you can learn a lot during a short period thanks to the informative guides!

20. Historic Chicago Tour

Run by Urban Kayak Chicago Riverwalk , the Historic Chicago Tour gives you a “duck’s” view of the beautiful Riverwalk as you paddle down the Chicago River. Along the way, you’ll stop at key points to learn more about the area’s history and architecture. Although there is a bit of boat traffic along the river (OK, a lot of boat traffic), the guides know how to keep everyone safe and it’s appropriate for even beginner kayakers.  If you prefer to go it alone, Urban Kayak also rents kayaks and paddleboards and offers classes to help you up your paddling skills.

21. Skyline Lake Tours

With unparalleled views over Lake Michigan and the city skyline, Shoreline Sightseeing Skyline Lake Tours offers breathtaking, 40-minute cruises covering six miles of the shoreline.  Some of the highlights of the tour include the Willis Tower (home of the Skydeck Observation Deck and formerly known as the Sears Tower), the John Hancock Center, the Field Museum, and the Adler Planetarium.  There is a bar on board to buy drinks and a pre-recorded track of interesting information playing throughout the ride. While this is a more general tour, they offer an architecture tour, as well. 

Tours depart from Navy Pier on the half-hour, with extra cruises sometimes added in spring and fall. Excursions are dependent on weather, so be sure to check times and availability before you go. Generally, there are no tours during colder months of the year.

22. Chicago Skyline Sail

There is something truly special about sailing. From the wind rushing through to sails to the sound of the waves lapping against the boat, it’s a relaxing experience and a great way to explore Lake Michigan.   Tall Ship Windy (love the name by the way) offers a Skyline Sail onboard a 148-foot four-masted schooner.  You can get sweeping views of the Chicago skyline from the deck of the boat during the 75-minute ride and the soaring skyscrapers create a mesmerizing juxtaposition to the traditional sailboat.  If you’re traveling with kids, make sure to check their list to see if they have any of their pirate-themed outings or fireworks cruises while you’re in town!

23. Seadog Lakefront Speedboat Tour

While sailboats and cruises are a great way to get out on Lake Michigan if you’re in the need for speed look no further than the Seadog Lakefront Speedboat Tour operated by City Cruises by Hornblower. As you whiz across the lake during this 30-minute ride, you can absorb the skyline views while you listen to the guides give vivid and entertaining descriptions of what you’re seeing.  Keep in mind that the boat is open-air, so you might get wet, and it’s probably best to avoid it during rough weather.

If you want to zip across the lake even faster then you can opt for their extreme thrill ride. Conversely, for a more leisurely option, you can opt for a brunch, lunch, or dinner cruise or try one of their special holiday-themed boat rides.  There are plenty of options to choose from so it’s a good idea to check out their website before deciding on a tour.

Ready to roam?

We hope that this list of the top tours and excursions in Chicago has left you inspired to pack your bags and head to the Windy City for your next vacation.  If you need more expert advice, make sure to check our lists of the Best Things to Do in Chicago and the 25 Best Day Trips From Chicago , or download our app and try any of our Chicago scavenger hunts . 

As always, we would love to hear your feedback and please let us know if we have missed any hidden gems! 

Happy hunting!

Frequently Asked Questions

Some of the most popular walking tours in Chicago include options from Free Chicago Walking Tours, scavenger hunt tours from Let’s Roam , and the Chicago Gangsters and Ghosts Tour.

If you’re planning some sightseeing in Chicago , don’t miss out on the intriguing crime tours, and be sure to hop on a boat cruise. Lastly, try at least one of the app-guided scavenger hunt tours from Let’s Roam !

There are many great boat tours in Chicago , including the Chicago Architecture Foundation River Cruise, the relaxing sunset cruise from Wendella Tours and Cruises, and the Urban Kayaks’ Historic Chicago Tour.

The Windy City is full of amazing pubs and grub! If you’d like to tour Chicago pubs , try Let’s Roam’s Chi-town Bar Crawl , the Chicago Prohibition Bus Tour, or the Historic Chicago Walking Bar Tour.

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Cruises & Tours

Explore chicago by land, water or air.

Whether you’re in town for just one day or are a life-long resident, cruises and tours of Chicago are a great way to see the sights, discover something new, or treat yourself to an unforgettable experience.

From laid-back sightseeing cruises and elegant dining cruises to heart-pumping thrill rides to upscale private charters, Lake Michigan and Chicago River cruises departing from Navy Pier offer a memorable experience for all.

Our Cruises & Tours

Architecture & Sightseeing Cruises

Take in Chicago’s iconic skyline and the scenic Chicago River with sightseeing cruises at Navy Pier! These fun experiences offer guests panoramic city views along with entertaining and enlightening commentary about Chicago’s architecture and history.

Brunch, Lunch and Dinner Cruises

When you dine on Like Michigan, every table is the best in the house. Navy Pier’s brunch, lunch and dinner cruises pair world-class cuisine with panoramic views of the city and lakefront.

Speedboat Tours and Thrill Rides

This isn’t your parents’ leisure cruise! On these 30-minute speed boat rides, you’ll tear across Lake Michigan at up to 45 miles per hour while getting entertaining and informative commentary on Chicago.

Specialty and Holiday Cruises

There’s always something worth celebrating with cruises on Lake Michigan and the Chicago River. Our partners offer themed cruises for major holidays, as well as a wide variety of special events that are sure to get you in the party mood.

Groups And Private Charters

Perfect for corporate outings and special occasions, group cruises and private charters offer unforgettable experiences for up to 800 guests.

Bicycle Tours

Bike & Roll Chicago allows guests to rent bicycles for a fun experience on the lakefront.

Cruise & Tour Types

Shoreline Architecture River Tours

Take Shoreline’s award-winning 75-minute Architecture River Tour to discover Chicago’s renowned landmarks as presented by our expert and entertaining guides. You’ll learn how Chicago rose...

City Cruises – Premier Dinner Cruise on Lake Michigan

Lake Michigan dinner cruises are the perfect setting for celebrating with friends, connecting with colleagues, or a romantic evening. Odyssey Lake Michigan dinner cruises are...

City Cruises – Premier Lunch Cruise on Lake Michigan

A two-hour Lake Michigan lunch cruise is the perfect way to enjoy time with family or the company of great friends. Retreat from a busy...

City Cruises – Signature Dinner Cruise on Lake Michigan

Celebrate a special occasion, host a group event or share a romantic evening aboard Spirit of Chicago. Great for parties of all sizes, a Spirit...

City Cruises – Spirit of Chicago Dinner Cruise

Catch the Chicago skyline at sunset during the most beautiful time of the year, and join us for a fun, laid-back, 2-hour cruise. Spirit's Lakefront...

City Cruises – Odyssey Lake Michigan Dinner Cruises

Odyssey Lake Michigan presents special prix fixe dinner cruises, offering guests the opportunity to try one of Chicago’s most unique dining experiences at an incredible...

City Cruises – Spirit of Chicago Brunch Cruises

Whether you’re a native Chicagoan, newcomer, or just visiting, a Spirit of Chicago brunch cruise is the perfect weekend outing. See well-known Chicago attractions from...

City Cruises – Signature Lunch Cruise on Lake Michigan

With the sunshine reflecting off the lakefront, there’s no better place to enjoy an afternoon in Chicago than aboard a lunch cruise. Departing from Navy...

City Cruises – Seadog River and Lake Architecture Tour

Enjoy Chicago’s iconic skyline with an exciting architecture cruise on the Chicago River. Departing from Navy Pier, this 75-minute narrated cruise is the best way...

City Cruises – Seadog Lakefront Speedboat Tour

Our Lakefront Speedboat Tour is the best way to view Chicago from the lake, combining an exciting speedboat ride along the shoreline with informative and...

City Cruises – Seadog Extreme Thrill Rides

With exhilarating high speeds and full 360° spins, this jet-propelled ride blasts off to start and splashes down to stop. Experience full throttle slalom runs,...

City Cruises – Odyssey Lake Michigan Brunch Cruise

This two-hour brunch cruise on Odyssey Lake Michigan, departing from Navy Pier, is ideal for capping off an incredible weekend. Enjoy a delicious menu stocked...

City Cruises – Odyssey Lake Michigan Groups

Host a truly unforgettable event on Lake Michigan. Book your group aboard one of Odyssey's regularly scheduled lunch or dinner cruises, or have an event...

Shoreline Sightseeing Group Tours

Adventures are meant to be shared. Turn your next family gathering or corporate outing into an awesome adventure by booking with Shoreline. We offer special...

City Cruises – Chicago Elite Private Events

It's your yacht. Let our professional event planners create a custom event just for your group aboard the Chicago Elite. With two fully enClosed ,...

City Cruises – Seadog Groups

Planning a special outing for your group? Charter Seadog for an event everyone will enjoy! With the ability to travel both the lake and river,...

Shoreline Sightseeing Water Taxis

Shoreline Sightseeing’s water taxis are a great way to get around town. Starting in May and running through September, our water taxi service offers fast...

City Cruises – Spirit of Chicago Group Cruises

Host an event unlike any other in the city! Book your group aboard one of Spirit’s regularly scheduled lunch, brunch, cocktail or dinner cruises, or...

City Cruises – Premier Brunch Cruise on Lake Michigan

Experience the city’s most unique floating event venue! City Cruises offers all-inclusive packages, chef-prepared menus, full bar options, and entertainment customized to fit your needs—all...

City Cruises – Signature Brunch Cruise on Lake Michigan

Shoreline Skyline Lake Tours

Shoreline’s 40-minute Skyline Lake Tour offers a relaxing way to experience the panoramic of the city’s famed skyline as seen from majestic Lake Michigan. The...

Tall Ship Windy Chicago Skyline Sail

Tall Ship Windy is closed for the season and will reopen in May 2024. Visit the Tall Ship Windy website to stay up to date...

Tall Ship Windy Private Charters & Weddings in Chicago

A Beautiful Stage for Your Event Set sail on Windy for weddings, parties, corporate functions, reunions, church outings, tour groups, team building and more! Windy...

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CHICAGO'S ORIGINAL ARCHITECTURE TOUR®

BEST SEAT IN THE HOUSE

Choose your adventure, chicago river architecture tour (90 minutes).

Take in the world-renowned architecture as our expert guides tell the story of 130 years of architectural innovation.

We like our drinks stiff, not our tour guides.

Chicago River Architecture Tour (45 minutes)

This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours.

The Ultimate Chicago experience.

We're In the People Business

This was one tour that I can honestly say was worth doing & probably should be a must do/ see on your visit to Chicago.

Ginette, 2023

We were recommended the architecture boat tour by a few locals and it was absolutely amazing!! Beautiful views from anywhere you sat and an extremely knowledgeable and funny tour guide led the trip. Great value for money and so so worth it. Thank you!!

Jessica W, 2024

The skyline was beautiful and the buildings all shined differently. Pictures come out amazing!

Christina, 2023

SEE FOR YOURSELF

Book your experience now.

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Reserve Your Spot with Confidence! Full Refunds with 24 Hrs Notice. Reschedule at any point, even after tour, if space allows!

Chicago Walking Tours

See our Calendar Below for All Tours, as well as Things to Do & Travel Tips

Featured tours, architecture tour, architecture tour highlights, haunted history, haunted history highlights, loop and millennium park, loop and millennium park highlights, riverwalk and history tour, riverwalk and history tour highlights, lincoln park & blues, lincoln park & blues highlights.

Magnificent Mile Tour

Magnificent mile tour highlights.

Tours by Foot offers walking tours and travel tips for your trip to Chicago (and other cities).

Expert guides offer local knowledge of the Loop, Millenium Mile, the Chicago Pedway, Lincoln Park, and more. They also provide local travel advice on the top things to do, how to get tickets, and what to do in Chicago tonight.

• Guided Walking Tours
• Free Self Guided Tours (researched and written by our professional guides)
• Audio Tours (researched AND recorded by the same guides!)

These exciting and informative sightseeing city tours will take you through many of the Windy City's most famous neighborhoods.

• Walking Tours
• Architecture Tours
• Tourist Discount Passes
• Chicago Travel Tips

CHICAGO WALKING TOURS

We provide a platform for local, freelance tour guides to lead walking tours as well as ghost and architecture tours so that you may enjoy a worry-free quality sightseeing experience.

Walking tours are our forte, and we offer several daily and weekly pay-what-you-like walking tours of Chicago and completely free self-guided options.

You can browse our tours by clicking the links below, scrolling through our public calendar (also below), or going directly to our  booking page . 

We have roughly 1000 reviews with a rating of 5 out of 5 stars, and 97% of reviewers rate us as very good or excellent.

We are so well-reviewed, yet TripAdvisor seems to hide us from you (probably because they can’t sell our tours for commission).   Read the reviews  for yourself.  

Our premiere Chicago walking tours are great day or night and serve as introductions to the city, Chicago history and cover the many of the main tourist attractions.   

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Our Regularly Scheduled Tours

• The Birth of the Skyscraper:  Architecture Tour is a great way to discover and appreciate the incredible landscape of buildings in Chicago and it ends in Grant Park near the famed Buckingham Fountain.
• The  Riverwalk and Chicago History Tour follows the path of the Chicago River and focuses on the history of Chicago, the Chicago Flag, and the beautiful buildings that line the river.
• North Loop and Millennium Park Tour , which covers a great portion of Chicago’s downtown Loop neighborhood, public art, and ends in Millennium Park.
• Our  Chicago Ghost Tour -Haunting History is for folks who love haunting history and creepy tales of the dark side of the White City.
• On The Magnificent Mile Tour , you will discover fun Chicago facts like the history of deep dish pizza while exploring our most popular downtown area.

Weekly Tours

• Our  Gold Coast Tour  meanders through the history of high society where you will be introduced to the glamorous residential neighborhood built around Lakeshore Drive.
• Explore Lincoln Park on our Lincoln Park and Gangster Tour to appreciate a unique neighborhood scattered with hidden history including tales of Chicago Gangsters.
• We also offer a West Loop tour which combines great storytelling for history buffs with great photo ops for those more in the “sightseeing” mood! 
• Get out of downtown and check out the Chicago Street Art on our Wicker Park Culture & Street Art tour.

Winter Tours

We offer tours year-round, even in Chicago's winter, but we take into account the need to be seasonably appropriate for walking tours. Check out our special Winter offers:

• In the winter, we offer a Pedway Tour that explores the indoor tunnels and paths to discover Chicago architecture and arts in a warmer way.
• There is also a  Winter Loop option where we will spend about half of the time outdoors looking up at the skyscrapers and the other half will be spent inside exquisite public buildings and lobbies.
• Our Winter Architecture Tour explores the unique landscape of buildings in the downtown area while also popping into many lovely lobbies for warmth!  This tour is abbreviated and adjusted for our Chicago winters.

En Español:

• Tour del North Loop y Millennium Park
• El Tour Chicago Riverwalk
• Audio Tours

CHICAGO ARCHITECTURE TOURS

Many of our pay-what-you-like walking tours are architecture tours or architectural points are a large part.

These tours include:

• The Birth of the Skyscraper
• North Loop and Millennium Park Tour
• Riverwalk and Chicago History Tour
• The Magnificent Mile Tour
• West Loop Tour

In addition to our walking tours, other walking tour companies offer excellent architecture tours.

Another popular option is to take an architectural boat cruise . There are even architectural tours by bus and Segway.

If you are on a budget or would like to take things at your own pace, then consider one of our self-guided walks .

OTHER TOURS

In addition to walking tours, Chicago has bus, bike & boat tours. Read all about them...

• What is the Best Chicago Architecture Tour?
• Chicago Boat Tours Compared
• Hop on Hop off Chicago Map | Understanding the Bus Routes
• Chicago Ghost Tours | Haunted Tours in the Windy City
• Chicago Segway Tours
• Chicago Bike Rentals and Tours

AUDIO TOURS

Can't make one of our guided tours?

That is no problem; we have recorded some of our best tour guides who give their tours and made them available to you anytime.  

Here is how it works:

• Purchase an Audio Tour
• Receive a confirmation email with details.
• Enjoy the tour(s).

Available Tours:

• Downtown Chicago ($2.99)

PRIVATE TOURS

We also offer our guiding services for private groups, families, or school groups where we can guide you in the Loop, the South Side and anywhere else in Chicago.

Find out more about private tours...

And much, much more

North america, united kingdom & ireland, middle east & india, asia & oceania.

Iconic Foods of Chicago Tour

Yes, chef chicago: a bear-inspired food tour, gateway to the west loop food tour, the chinatown adventure food tour, street foods of pilsen, buildings and bites.

• Compare Tours
• Bachelorette / Bachelor

Celebrations

Group travel.

Chicago’s Original Food & City Tour

Real deal chicago food.  iconic eats & fresh hot spots..

Private Experiences

Corporate Groups

Bachelorette Parties

• Multi-Day Itineraries
• Step-On Guides

Welcome to My Chicago. It’s Delicious Here.

Frequently Asked Questions

Will local chicagoans enjoy your tours.

Absolutely! More than half of our guests are local to the Chicagoland area, and they always say the same thing: “I learned so much about Chicago’s history and restaurant scene that I didn’t know!” Locals who come on our tours will find their new favorite date night spot, and can impress their visiting friends with all their Chicago “insider” knowledge.

I hate feeling like a tourist. Will the guide have a bullhorn and an umbrella?

Yeah, we hate that, too. And, no, no umbrellas or bullhorns. Our guides feel more like part of the group. They’re friendly without being annoying, and they don’t just recite a script. We hire people who love this city, and we train them extensively to make their job look effortless. No cringey tourist stuff, we promise.

This seems like a lot to spend on sample bites. How much do we get to eat?

No need to make reservations for after the tour. You’ll enjoy the equivalent of a full meal or more on our food tours.

What happens if it rains or snows?

Rain or shine, you gotta eat! Unless the weather looks like it’ll threaten the safety of our guests or guides, the tours will run in most conditions. If it’s too wet or cold, we’ll just spend more time indoors at our restaurant partners. And we’ve got some snazzy ponchos for you just in case.

Can you accommodate my dietary restriction?

If you let us know when you book your tour, we CAN provide vegetarian-friendly tasting, but we CANNOT offer alternatives or substitutions for any other allergies (including lactose intolerant) or dietary restrictions (including vegan and gluten free). Vegetarian-friendly options must be requested in advance during the ticket purchase process.

Go Ahead. Raise Your Expectations.

Better call dibs. our chicago food tours fill up quick, chicago
food &
city tours.

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Vote in Condé Nast Traveler Reader’s Choice Awards to make Chicago the Best Big City in the country for a historic eighth year in a row.

The Bean is back

Chicago’s iconic “The Bean” sculpture has re-opened just in time to celebrate Millennium Park’s 20th anniversary season.

Sundance x Chicago

Experience groundbreaking cinema during Sundance x Chicago, with Midwest premieres of exciting films, insightful panel discussions, and exclusive master classes.

Get tickets today

Pride Month

Chicago goes all out to celebrate Pride, with massive festivals, a joyous parade, and more inclusive events all month long honoring LGBTQ+ history and culture.

Explore Pride events in Chicago

Summer in Chicago

Summer is here in Chicago! Discover the best things to do, including can’t-miss events, waterfront adventures, top exhibits, and so much more.

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See the city through the eyes of the people who know it best — Chicago locals. Read our blog for insider tips and guides.

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Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States

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28 Fun Things to Do in Chicago

Chicago shines for its world-class museums, various shopping districts, vibrant neighborhoods and lively nightlife venues. Explore the city's innovative roots at the Griffin Museum of Science and Industry, where you can walk inside the U-505

• All Things To Do
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Millennium Park and Cloud Gate Millennium Park and Cloud Gate free

U.S. News Insider Tip: Construction around the Cloud Gate sculpture will limit the public's access to this top tourist attraction until spring 2024. While you might not be able to snag a selfie with "The Bean," many other attractions are available within the park. – Cortney Fries

A first-time visit to Chicago isn't complete without a stop at Millennium Park. Situated in the Loop just north of the Art Institute of Chicago , this 25-acre space is used to showcase cutting-edge art, architecture and landscaping; it also acts as a backdrop for concerts and festivals.

Grant Park and Buckingham Fountain Grant Park and Buckingham Fountain free

U.S. News Insider Tip: If you're visiting Chicago Sept. 8 through 10, head to Grant Park early – around 11 a.m. to avoid the lines – for the Taste of Chicago. Enjoy the park and eat the best cuisine the city has to offer. Admission is free. – Sarah Estime

Often referred to as "Chicago's front yard," Grant Park is an approximately 313-acre swath of green space that starts at the eastern edge of the Loop and stretches down to the northern fringes of the Near South Side.

Art Institute of Chicago Art Institute of Chicago

Home to one of the country's most impressive collections of impressionist and post-impressionist art (plus works from numerous other genres), the expansive Art Institute of Chicago features nearly 300,000 works from all over the world in its permanent collection. You'll find pieces created in the Byzantine era, as well as paintings completed just a few decades ago.

Highlights include Jacob Lawrence's "The Wedding," Georgia O'Keeffe's "Sky above Clouds IV" and Grant Wood's "American Gothic." The Art Institute's exhibits also include all sorts of intriguing artifacts, from European armor to the Thorne Miniature Rooms, which showcase interior design and furnishings in Europe and America from the late 13th to early 20th centuries. In addition to the permanent collection, the Art Institute hosts traveling exhibitions covering a variety of subjects and showcasing a diverse array of artists and genres.

Popular Tours

Chicago Architecture River Cruise

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from $ 53.70

Chicago River 90-Minute Architecture Tour

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Chicago River 45-Minute Architecture Tour from Magnificent Mile

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The Magnificent Mile The Magnificent Mile free

U.S. News Insider Tip: The Magnificent Mile, known for its world-class shopping, also has plenty to offer architecture buffs. Book a walking tour with the Chicago Architecture Center and hear the untold stories of North Michigan Avenue's architectural icons. Tours start at $30. – Sarah Estime

For shopping at more than 450 retailers within walking distance in downtown Chicago, make your way to The Magnificent Mile.

Navy Pier Navy Pier free

Extending out onto Lake Michigan, Navy Pier offers plenty in the way of family-friendly entertainment.

The first thing you'll spot once you set foot on the pier is the towering Ferris wheel (which stands 196 feet tall); you'll also find a drop tower and a carousel. Once the kids have had their fill of thrill rides, you can spend some time cruising the Chicago River on a sightseeing or speedboat tour or spend a few hours exploring the Chicago Children's Museum , with hands-on exhibits ranging from treehouses to fire trucks.

Lincoln Park Zoo Lincoln Park Zoo free

U.S. News Insider Tip: North Avenue Beach is a short walk over the North Avenue Bridge when you park at the southern end of the Lincoln Park Zoo lot. Explore the zoo, then stroll over to the beach for an afternoon in the sand. – Cortney Fries

Located 2 miles north of the Loop in the North Side neighborhood of Lincoln Park, the Lincoln Park Zoo is home to nearly 200 species, such as zebras, sloths and hippos. Visitors can view the zoo's furry (or scaly) friends in their natural habitats: Check out the gorillas in the sprawling, award-winning Regenstein Center for African Apes, or head to the Kovler Seal Pool to get up close and personal with harbor seals. Seal training and feeding occurs daily at 11:30 a.m. and 2 p.m.

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360 CHICAGO Observation Deck 360 CHICAGO Observation Deck

One of Chicago's most notable attractions is its skyline, and one of the best places to experience it is at the 360 CHICAGO Observation Deck.

Formerly known as the John Hancock Observatory, 360 CHICAGO towers 1,000 feet over The Magnificent Mile from its location on the 94th floor of the John Hancock Center (or 875 North Michigan Avenue as its more formally known). Encased by floor-to-ceiling windows, 360 CHICAGO boasts expansive views of the city; on a clear day, you can see four states. Meanwhile, the interactive screens will help you identify different landmarks that appear in your panorama.

The Field Museum The Field Museum

U.S. News Insider Tip: After hours of museum hopping, grab a kid-approved lunch at Kim & Carlo's Hot Dog Cart. The no-frills stand offers everything from vegan dogs to the traditional Chicago hotdog. Enjoy your lunch on the water. – Sarah Estime

This extensive natural history museum occupies half an acre of Grant Park 's Museum Campus and houses exhibits that showcase artifacts from multiple eras and destinations, making it a must-see for kids (as well as any fans of the "Indiana Jones" movies).

Chicago Lake and River Architecture Tour

(1768 reviews)

Lake Michigan Sunset Cruise in Chicago

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Chicago Architecture Center River Cruise aboard Chicago's First Lady

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from $ 54.00

Chicago Architecture River Cruise Chicago Architecture River Cruise

A visit to 360 CHICAGO or Skydeck Chicago will give you a good overview of the city's layout. But if you want to learn more about Chicago's sky-high buildings, tag along on an architecture river cruise. During a river cruise, you'll gain great views and historical insight about well-known structures like the Wrigley Building, the Leo Burnett Building and the Fulton House.

Though several companies, including Wendella Sightseeing Co. and Chicago Line Cruises, offer architecture river cruises, most travelers recommend climbing aboard a Chicago's First Lady Cruises boat with a Chicago Architecture Center docent. You'll learn tons of information about the area's architecture, plus catch superb skyline photo-ops.

Maggie Daley Park Maggie Daley Park free

U.S. News Insider Tip: There are many restaurant options around the park, but Wildberry Pancakes & Café is a satisfying brunch spot. Choose from creative pancake options, a variety of omelets, crepes, sandwiches and salads. Go hungry and leave happy. – Cortney Fries

Opened in 2014, Maggie Daley Park is an expansive property located just east of Millennium Park in downtown Chicago.

Griffin Museum of Science and Industry Griffin Museum of Science and Industry

U.S. News Insider Tip: Mid-November through the first week of January, experience the annual "Christmas Around the World" and "Holidays of Light" exhibits. Volunteers decorate more than 50 trees in celebration of holiday traditions from around the globe. – Cortney Fries

Chicago's extensive Griffin Museum of Science and Industry is the Western Hemisphere's largest science museum, showcasing more than 35,000 artifacts and a variety of hands-on exhibits meant to inspire creativity. The museum resides in the 14-acre former Palace of Fine Arts, which hosted the famous World's Columbian Exposition in 1893. The fair brought together some of the world's greatest scientific minds, including Thomas Edison and Nikola Tesla, who at the time were competing to prove which type of electricity – direct current or alternating current – was more effective. 

Wrigley Field Wrigley Field

U.S. News Insider Tip: If you're visiting during the holiday season, don't miss Winterland at Gallagher Way for family-friendly rides and games inside and around the ballpark. Christkindlmarket Wrigleyville is free to enter. Enjoy festive shopping and international food and beverage selections. – Cortney Fries

Chicagoans take their love of sports very seriously. So, for a real taste of Chicago culture, head north of the Loop to Wrigley Field to watch the Chicago Cubs play ball at the Friendly Confines. History buffs will also appreciate this sports treasure, which first opened in 1914 and holds the honor of being the second-oldest Major League Baseball stadium in the country (after Fenway Park in Boston ).

Shedd Aquarium Shedd Aquarium

U.S. News Insider Tip: If you're visiting in the summer (June through August), check out Jazzin' at the Shedd. You can enjoy jazz music and drinks with incredible views from the terrace. Plus, the lights dim in the aquarium for a unique experience. – Elizabeth Von Tersch, Senior Editor

Shedd Aquarium is one of the world's largest indoor aquariums, housing around 32,000 creatures. While you're here, you can feel stingrays float beneath your fingers, listen to sea lions bark and learn all about a variety of turtles. A visit to Shedd Aquarium will lead you through a cornucopia of habitats, where you'll find additional animals like penguins, piranhas, sharks and beluga whales. Or, for an additional fee, you can participate in specialty experiences like animal encounters, feeding experiences and virtual reality.

360 CHICAGO Observation Deck Admission

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Chicago River Architecture Tour with Small Boat Upgrade Option

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Chicago: Gangsters and Ghosts Walking Tour

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The Chicago Riverwalk The Chicago Riverwalk free

U.S. News Insider Tip: During the summer, there is nothing better than watching the boats go by as you relax at City Winery Riverwalk Wine Garden. Rent a retro boat from Chicago Electric Boat Company and cruise the river yourself. – Cortney Fries

When the weather warms up in Chicago, there are few better places to enjoy the outdoors than the Chicago Riverwalk. The 1.25-mile pedestrian walkway on the south bank of the Chicago River is the perfect place to take a stroll and observe the city skyline. Plus, there are numerous activity options to enjoy directly on the water, such as a boat or kayak tour . If you prefer to explore on your own two feet, visit the public gardens and art displays, or grab a meal at a popular restaurant or bar overlooking the Chicago River. And if you want to learn more about the river's unique history, check out the McCormick Bridgehouse & Chicago River Museum, which celebrates the city's famous movable bridges. What's more, Art on theMART – a massive digital art projection on the facade of theMART (formerly The Merchandise Mart) – is best viewed from the Riverwalk.

Skydeck Chicago at the Willis Tower Skydeck Chicago at the Willis Tower

More than 1.7 million people make their way to Willis Tower's Skydeck Chicago each year, and it's easy to see why. Occupying the 103rd floor – that's nine floors higher than 360 CHICAGO – of the 110-story Willis Tower (the third-tallest building in North America after One World Trade Center and Central Park Tower), Skydeck Chicago boasts breathtaking views of the city. Visit on a sunny day and you may be able to see far beyond Chicago's borders to Indiana, Michigan, Wisconsin and other parts of Illinois.

The highlight for most visitors is the Ledge. Extending 4.3 feet beyond the building's exterior, this platform is made entirely of glass – even the floor. Travelers also liked the video screens that show what it would be like to stand 103 floors above other Chicago attractions, including Wrigley Field and Millennium Park . However, long lines quickly form for Skydeck Chicago, so plan on arriving early or purchasing a Chicago CityPASS, which covers expedited admission into the attraction. Or, simply pay extra for expedited entry, which features an express line to the elevators. For the best views, it's advised that you visit just after opening or after sunset. If you'd like to enjoy the sunset from the tower, plan on arriving 30 to 45 minutes before sunset to ensure you have enough time to get through the elevator line and up to the top.

North Avenue Beach North Avenue Beach free

Located in Lincoln Park directly on Lake Michigan, North Avenue Beach is one of the most popular swimming spots in Chicago.

The sandy beach has volleyball courts, plenty of space for visitors to stretch out and multiple things to do near nearby. Plus, it offers spectacular views of the city skyline. Beachgoers can also find restaurants, sports rental companies, restrooms and more inside a 22,000-square-foot beach house adjacent to the shore.

The Second City The Second City

If you've seen a sketch comedy show or hilarious movie in the last 40 years, it's likely that someone from The Second City appeared in it. The Second City is one of the world's most iconic improvisational comedy theaters, and it has helped launch the careers of numerous famous comedians, including Bill Murray, Tina Fey, Keegan-Michael Key, Steve Carell and Stephen Colbert. If you're in the mood for a laugh, check out a live show on any night of the week at any number of The Second City's seven stages (which are all housed in its facility at the northwest corner of North Avenue and Wells Street in Old Town). 

Recent reviewers said that everyone in their group could not stop laughing during the shows, which typically last 90 minutes to two hours. Ticket prices vary by the show and date, but run anywhere from $30 to $100.

The Chicago Theatre The Chicago Theatre

Aside from Cloud Gate and Buckingham Fountain , The Chicago Theatre's red and yellow marquee is perhaps one of the city's most recognizable landmarks. Illuminating North State Street at the northern edge of the Loop, The Chicago Theatre first opened its doors in 1921 as an extravagant movie theater and performance venue. Throughout its history, the theater has hosted such big names as Duke Ellington, Diana Ross and Prince, in addition to screening blockbuster flicks. Though the theater fell into disuse in the 1970s, new management and a full renovation in the 1980s helped return the venue to its former glory. Today, the theater is still used for a variety of comedic, theatrical and musical performances.

According to past patrons, the theater's historic appearance enhances the overall experience of catching an event here. Just remember, cameras and video cameras, including those on cell phones, cannot be used during tours or performances.

Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour by Open-Top Bus

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Chicago Favorites Ultimate Food and Walking Tour

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Chicago Children's Museum Chicago Children's Museum

Located at Navy Pier , the Chicago Children's Museum offers temporary and permanent play-based exhibits for babies, toddlers and kids ages 4 and older. Founded in 1982 by the Junior League of Chicago as a response to cuts in arts programming, the museum was originally housed in two hallways of what is now called the Chicago Cultural Center . Today, children can dig for "teeth" and "bones" in "Dinosaur Expedition," climb through tunnels of "Cloud Buster," test their STEAM (Science, Technology, Engineering, Art and Math) skills in the Tinkering Lab and paint, draw or sew in the art studio.

Recent visitors appreciated the interactive, hands-on exhibits, which they recommend for young children.

American Writers Museum American Writers Museum

U.S. News Insider Tip: Across the street from the museum, you will find the first Nutella Café, where you can savor French and Italian dishes featuring the heavenly hazelnut spread. The gelato is roll-your-eyes-to-the-back-of-your-head good. – Cortney Fries

The first museum in the United States dedicated to celebrating the diverse voices and influence of American authors, the American Writers Museum is an interactive journey through more than five centuries of written and spoken word. This relatively small museum, which opened in 2017, features thoughtful and reflective exhibits that you can touch, smell, hear and see. 

DuSable Black History Museum and Education Center DuSable Black History Museum and Education Center

U.S. News Insider Tip: If driving in Chicago isn’t your thing, consider taking the No. 55 bus to the museum. The bus drops you off within just a five-minute walk of the museum. – Sarah Estime

The DuSable Black History Museum and Education Center, named for Jean Baptiste Pointe DuSable, the entrepreneur who is credited with founding Chicago, is a must-visit for anyone looking to learn more about African American history in the city of Chicago and America. It celebrates its 62nd anniversary in 2023, and is full of thought-provoking exhibits, including those that showcase fine art created by influential African American artists and historical materials. Note that visitors hoping to enjoy “The March” exhibit, an immersive experience depicting the historic March on Washington and Martin Luther King Jr.'s "I Have A Dream" speech, can go in groups of no more than four at a time.

Adler Planetarium Adler Planetarium

The first planetarium in the Western Hemisphere, the Adler offers unrivaled insights into our solar system. Indeed, "Our Solar System" is one of its permanent exhibits, along with "Mission Moon," "The Universe: A Walk Through Space and Time," "Telescopes: Through the Looking Glass" and "Astronomy in Culture," among others. Its facilities include the Doane Observatory, which has the largest telescope available to the public in the Chicago area, through which visitors can glimpse celestial objects trillions of miles away. The Adler also has three full-size theaters – the 3D Universe Theater, the Definiti Space Theater and the Grainger Sky Theater – in which it screens programs like "Destination Solar System," "Planet Nine" and "One World, One Sky: Big Bird's Adventure."

Space enthusiasts invariably find the Adler's presentations both informative and entertaining, if somewhat pricey. Most visitors suggest setting aside a few hours to explore the various exhibits and shows. Travelers recommend maximizing your parking expenses by also visiting the Shedd Aquarium or The Field Museum , which also sit on the Museum Campus. Reviewers also appreciated the Lake Michigan and skyline views as seen from the planetarium.

Offbeat Street Art Tour Offbeat Street Art Tour

U.S. News Insider Tip: If you’re looking for unique souvenirs from your Chicago trip, consider The Goddess & Grocer for its gift baskets. – Sarah Estime

In Chicago, you can find eye-catching street art nearly everywhere. As you sightsee, you’ll be greeted with unique, thought-provoking art on the sides of buildings and underneath bridges. If you’re looking for an experience that walks you through the history and cultural significance of Chicago's street art scene, look no further than the Offbeat Street Art Tour. On this two-hour tour, you’ll discover new artists and learn the inspiration behind their colorful works, along with some interesting neighborhood history. You’ll also be able to take great photos along the way.

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The Green Mill The Green Mill

U.S. News Insider Tip: For visitors looking for a bite to eat after a night of jazz music, head across the street to Damera for an authentic Ethiopian meal, or down the block to the Fat Cat for a burger. – Sarah Estime

Best known for serving gangsters during its speakeasy days, the Green Mill invites travelers to step back in time. The long bar that runs along the club's left side sits in front of smokey mirrors and is peppered with decor reminiscent of the Prohibition era. The entire place is cast in a warm reddish glow while old-time jazz plays from the jukebox. The bar – one of Al Capone’s favorites – has no set menu; order whatever cocktails you like (though the chocolate martinis are delicious). There is also a selection of beer and wine.

Garfield Park Conservatory Garfield Park Conservatory free

One of the biggest botanical conservatories in the United States, the Garfield Park Conservatory houses thousands of plant species in eight indoor gardens, as well as 10 acres of outdoor gardens.

Each indoor space has a distinct focus. The Aroid House features varieties of its namesake, which are among the most popular houseplants; it also features sculptures by the world-renowned glass artist Dale Chihuly made specifically for the Aroid House. As its name suggests, the Desert House boasts cacti and succulents, while the Fern Room arranges ferns around an indoor lagoon. The Palm House, the conservatory's largest structure, recreates a tropical landscape complete with more than 70 palm trees. Meanwhile, the Elizabeth Morse Genius Children's Garden aims to educate little ones about plants. Horticulture Hall displays a range of flowers and plants and also has tables where visitors can take a seat and have a rest.

The Richard H. Driehaus Museum The Richard H. Driehaus Museum

Occupying a restored mansion built in 1883, the Richard H. Driehaus Museum presents exhibitions relating to architecture, art and design from the 19th century to the present day.

The Nickerson Mansion containing the museum boasts an entrance hall made with so much marble that the building was nicknamed "the Marble Palace." (The museum takes its current name from the philanthropist who founded it in 2003.) Its reception room features intricate woodwork as well as items from the museum's permanent collection, such as a Tiffany Studios lamp that dates back to the early 1900s. Meanwhile, the front parlor displays Renaissance Revival furniture original to the Nickerson Mansion. The dining room, fitted with elaborately carved oak, houses a silver punch bowl first exhibited at the 1893 World's Columbian Exposition. Other highlights from the permanent collection include a gem-encrusted inkstand, a ceramic clock, multiple chandeliers, paintings, sculptures and an array of decorative items.

Chicago Cultural Center Chicago Cultural Center free

The "People’s Palace," a popular destination occupying a full city block in the downtown Loop neighborhood, is a stunning architectural marvel as well as a venue for a great deal of cultural programming, including art exhibits and concerts. Among its features are one of the largest Tiffany stained-glass domes in the world (made with around 30,000 individual pieces of glass) and a marble lobby adorned with mosaics made of gold, glass and precious stones.

Visitors invariably rave about the impressive structure and its elaborate decorations, saying it’s worth it to pop in for free to see the ornate ceiling.

University of Chicago University of Chicago free

Founded in 1890 by John D. Rockefeller, the University of Chicago is an urban research university in the city's Hyde Park neighborhood close to Lake Michigan. Currently, it has more than 7,000 undergraduate students and more than 10,000 graduate, professional or other students as well as nearly 2,400 full-time faculty members.

Impressive as those statistics may be, they aren't reasons to visit. But the university's 217-acre campus, which was designated a botanic garden in 1997, and its mixture of English Gothic and modern architecture are. Some of the newer structures were designed by celebrated architects like Ludwig Mies van der Rohe and Eero Saarinen, while some of the older ones are adorned with gargoyles that date back to the 1893 World Columbian Exposition. The university welcomes visitors to explore its campus, and provides information about its architecture on its website. Those who've visited before routinely call the buildings diverse and beautiful, and many recommend stopping by in the spring when flowers bloom across campus, or fall when amber leaves transform the grounds.

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Watch CBS News

Justin Timberlake breaks his silence at Chicago tour stop: "It's been a tough week"

By Kerry Breen

June 22, 2024 / 10:02 AM EDT / CBS News

Just days after his arrest for allegedly driving while intoxicated , Justin Timberlake took the stage for the first of two concerts in Chicago. 

Between songs on Friday, he appeared to address the Sag Harbor arrest. Social media videos from the event show him addressing the audience. 

"We've been together through ups and downs, lefts and rights. It's been a tough week, but you're here, and I'm here," he said, before bowing to cheering fans. 

“It’s been a tough week” - Justin Timberlake pic.twitter.com/rIp2LZpZHs — Zach Moss (@zachlmoss) June 22, 2024

"I know I'm hard to love sometimes but you keep loving me right back," Timberlake added. 

Timberlake was arrested on Tuesday in Sag Harbor, Long Island. The singer was stopped at 12:37 a.m. local time after he allegedly drove through a stop sign, according to court documents reviewed by CBS News. Timberlake also allegedly failed to keep to the right side of the road, according to court documents. 

Timberlake allegedly told police that he had "one martini" and was following friends home, but the officer who pulled him over said that the singer was "in an intoxicated condition," with "bloodshot and glassy" eyes, and a "strong odor of an alcoholic beverage on his breath." He also allegedly "performed poorly on all standard field sobriety tests." Documents reveal that Timberlake refused three breath tests. 

Timberlake was arrested and his mug shot was taken. Timberlake was arraigned on Tuesday morning and released on his recognizance. He will make a virtual appearance in court again on July 26, officials said. 

The Chicago concerts are his first public appearances since the arrest. The stops are part of his Forget Tomorrow World Tour, his first major tour in five years. He will play a second concert on Saturday night. 

• Justin Timberlake

Kerry Breen is a news editor at CBSNews.com. A graduate of New York University's Arthur L. Carter School of Journalism, she previously worked at NBC News' TODAY Digital. She covers current events, breaking news and issues including substance use.

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• Start Me Up Play Video
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• It's Only Rock 'n' Roll (but I Like It) Play Video
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• She's a Rainbow ( fan-voted song ) Play Video
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Note: The other options for the fan-voted song were "Bite My Head Off," "Fool to Cry," and "She's So Cold."

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‘Hard to love’ Justin Timberlake talks DWI arrest at Chicago show: ‘It’s been a tough week’

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Justin Timberlake knows he’s “hard to love” sometimes but thanked his fans in the Windy City on Friday for doing so anyway, addressing his recent arrest in the Hamptons and subsequent charge of driving while intoxicated in public for the first time.

Apparently, his Tuesday arrest in New York did not “ruin” his world tour after all.

The Grammy and Emmy Award winner, 43, delivered a short but emotional speech Friday night at the United Center in Chicago, the latest stop on his Forget Tomorrow World Tour, as seen in concert footage posted on social media. As the boisterous crowd cheered him on, the former ‘N Sync frontman seemingly humbled himself in front of the sold-out arena .

“We’ve been together through ups and downs and lefts and rights. And, uh, it’s been a tough week. But you’re here and I’m here. Nothing can change this moment right now,” the singer said while holding an acoustic guitar and bowing to his adoring fans. “I know sometimes I’m hard to love, but you keep on loving me and I love you right back. Thank you so much.”

“Now if you’ll oblige me, I’d like to have a little sing-along with you guys,” he added, before launching into the show.

Justin Timberlake charged with driving while intoxicated in New York’s Hamptons

Justin Timberlake was arrested early Tuesday on New York’s Long Island on suspicion of driving while intoxicated. He was arraigned later in the day.

June 18, 2024

The “Can’t Stop the Feeling” singer was arrested on Long Island after Sag Harbor police saw his gray 2025 BMW UT run a stop sign and struggle to stay in its lane. Police who pulled him over just after 12:30 a.m. alleged the singer’s eyes “were bloodshot and glassy” and “a strong odor of an alcoholic beverage was emanating from his breath.”

“[H]e was unable to divide attention, he had slowed speech, he was unsteady afoot and he performed poorly on all standardized field sobriety tests,” according to court papers obtained by The Times. The “Rock Your Body” singer was booked and held overnight in jail, where his mug shot was taken. He was arraigned hours later in Sag Harbor Village Justice Court, on the eastern end of Long Island, the Suffolk County district attorney’s office confirmed to The Times. He pleaded not guilty, the New York Times reported.

Timberlake’s spokespeople and his attorney did not immediately respond to the Los Angeles Times’ requests for comment.

In surveillance footage obtained by CNN , a car that matched the police description of Timberlake’s vehicle could be seen running the stop sign near where Timberlake was arrested, but it did not appear to be swerving in the clip.

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“The Social Network” and “Trolls” actor had been having dinner and drinks with friends at the American Hotel and was pulled over about a mile away, where he told police officers that he had had only one martini before following his friends home. He refused to take a breath test three times and “performed poorly” on field sobriety tests, police said .

Page Six , citing anonymous sources, reported that the police officer who arrested the singer “was so young that he didn’t even know” who the 10-time Grammy winner was. Another source told the outlet that when he was pulled over, “Justin said under his breath, ‘This is going to ruin the tour.’ The cop replied, ‘What tour?’ Justin said, ‘ The world tour .’ ” The remark went viral Tuesday and, along with Timberlake’s mugshot, instantly became a meme.

At the police station, where he spent the night, he handed over his wedding ring, phone, baseball cap, watch and wallet, along with a vape pen and green and blue papers, the kind used for rolling marijuana, according to the New York Times.

“He was freaking out and stayed up all night when he was in custody,” a source told People on Friday. “He’s insisting he only had one drink and it wasn’t some wild night out.”

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Timberlake was charged with misdemeanor driving while intoxicated because he refused to take a breath test when he was pulled over, Timberlake’s attorney Eddie Burke Jr. told Us Weekly . The singer was also given two citations, one for running a stop sign and the other for not traveling in the correct traffic lane, Burke said.

He was released on his own recognizance; no bail was set. His next court date will be July 26 — the same day he is scheduled to be in Kraków, Poland, on his Forget Tomorrow tour. Timberlake‘s arrest took place during a brief break on the tour, which stopped in L.A. last month and will run through December.

He has kept a low profile since the incident. His attorney on Wednesday told TMZ that he and the singer look forward “to vigorously defending Mr. Timberlake against these allegations. He will have a lot to say at the appropriate time.” The outlet also reported that the musician, who does not have a previous arrest record, does not plan to check into a rehab facility — a proactive move often used by celebrities to look good in front of a judge and strike a better plea deal in alcohol- or drug-related legal incidents.

The remarks he delivered Friday in Chicago marked the first time Timberlake publicly acknowledged the arrest since it happened.

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After releasing his sixth studio album, “ Everything I Thought It Was,” in March, the hitmaker set off on his Forget Tomorrow world tour in April. The tour is scheduled to continue in Chicago on Saturday before he plays Madison Square Garden in New York on Tuesday and Wednesday.

The musician landed in hot water last year amid revelations in “The Woman in Me,” his ex-girlfriend Britney Spears’ bombshell memoir, that she had an abortion at Timberlake’s behest while they were dating around the turn of the century. Timberlake’s connection to Spears was also scrutinized in 2021 when a series of documentaries about her protracted conservatorship revisited the media’s treatment of the embattled pop princess , which included accepting his spin on their breakup.

Timberlake — now a father of two boys with actor Jessica Biel — took a lot of heat during that time, prompting a public apology to Spears and to his 2004 Super Bowl co-headliner Janet Jackson that acknowledged he “fell short” and benefited from “a system that condones misogyny and racism.”

In the wake of Timberlake’s arrest, Spears’ fans rallied to send her 2011 song “Criminal” — believed to be an allusion to her relationship with Timberlake — back up the charts . Her fans had some success with that endeavor back in January when they staged a digital-music coup to dethrone Timberlake’s new single “Selfish” by streaming her 13-year-old song with the same name.

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The swaggering showman is allegedly having a harder time lately landing roles in Hollywood, Page Six reported, and is facing lackluster sales for his tour and latest album, which dropped off the Billboard 200 chart after four weeks.

“The album didn’t do too well, and I don’t see Justin getting big acting roles right now,” a Hollywood insider told the outlet earlier this week.

“He’s got a bit of an ego,” another industry insider added. “His golden boy image is definitely depleted.”

Meanwhile, the owner of the American Hotel told TMZ that Timberlake would be welcomed back anytime, because he was a model customer, “great guest and a nice guy.”

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Likewise, “CBS Mornings” host Gayle King defended the musician Wednesday on air, saying that Timberlake is “a really, really great guy” and adding that the incident was “clearly a mistake” and that she bets “nobody knows it more than he.”

“He’s not an irresponsible person, he’s not reckless, he’s not careless,” King said. “Clearly this is not a good thing, he knows that.”

Other celebrities have either come out against the singer or come to his defense. Comedian Ricky Gervais used the viral news story as a way to plug his own vodka brand on X. But singer Billy Joel, who was spotted at the American Hotel after Timberlake’s arrest, told a New York news station, “Judge not lest ye be judged.”

On TikTok, footage from Timberlake’s May tour stop in Las Vegas began making the rounds, with users commenting on the crooner’s reddish eyes while performing in the clip and speculating about whether that was a precursor to his Sag Harbor arrest.

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