Chicago
Group Activities

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Our most recommended Chicago Group Activities

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

1. Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 2.5-hour guided walk, you'll get to taste the foods Chicago is best known for doing right. Enjoy deep-dish pizza, the original Italian pastries, Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional fee. Along the way, you’ll see some of Chicago's most iconic spots including Millennium Park, the Chicago Riverwalk, the Art Institute, and the famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels.

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Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

2. Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Spend an evening visiting the Chicago speakeasies that have been open since the Prohibition Era in the 1920s, many preserved in their original conditions. With your own private group, enter by way of secret entrances and enjoy the same cocktails ordered by infamous Chicago gangsters and bank robbers at these venues nearly a century ago. Relive the glamor of the 1920s while listening to stories of the rampant racketeering and bootlegging of the era.   Alcohol is available for purchase at the three to four different speakeasy stops. Your private tour guide will make Prohibition Era drink recommendations and tell you the stories behind them. Travel around with your young, professional guide and be chauffeured in luxury transportation, ranging from a luxury SUV to a full-sized luxury motor coach.

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Chicago: 1-Hour Escape Room Adventure

3. Chicago: 1-Hour Escape Room Adventure

The concept is simple, but the game is anything but — enter a series of elaborately designed rooms, you and your group must work together to find clues and crack codes to complete your mission. Escaping will require teamwork, communication, wits, and a sense of adventure. With five thrilling adventures to choose from, you may find yourself as a spy sent to recover a stolen painting or a falsely-accused prisoner determined to break out of jail. Once you arrive, a dedicated game guide will take you to your adventure and help you as needed. You will have exactly 60 minutes to complete the mission in your adventure and escape. No matter your choice of game, keep your wits about you and focus: you’ve only got one hour. After you and your group have emerged victorious, you’ll be conveniently located in River North, so you can easily celebrate with a bite to eat.

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Chicago: 1.5-Hour Open-Top Double-Decker Night Tour

4. Chicago: 1.5-Hour Open-Top Double-Decker Night Tour

From the top deck of a double-decker bus, experience Chicago at night. Enjoy a 75-minute, live-guided panoramic tour and take in unique views of the Chicago Skyline, comprised of world-famous skyscrapers and revolutionary architecture. Take a photo overlooking downtown from the Museum Campus in front of the Adler Planetarium. Be amazed by the beautiful water and light display of The Buckingham Fountain as you discover the bustling nightlife of Chicago. Marvel at the magical light show of the one-of-a-kind Art on the Mart, displayed on the facade of the Merchandise Mart. See the city reflect off of The Bean (Cloud Gate) at the famous Millennium Park. Experience the city that built the skyscraper and see architectural marvels like 875 N Michigan Ave (formally the John Hancock Building), the Wrigley Building, the Chicago Tribune Building, and the Willis Tower. End the tour at the Chicago Riverwalk, with the knowledge that you can continue exploring the city with confidence. From the pioneering skyscrapers, to the Great Chicago Fire, this night tour will take you on a journey you won't soon forget. Be sure to soak up the exciting atmosphere that makes the Windy City such a fascinating and dynamic place.

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Chicago: Bikes, Bites, and Brews Biking Tour

5. Chicago: Bikes, Bites, and Brews Biking Tour

Working up an appetite won’t be a problem on this signature bike tour combing city sightseeing with the best foods and brews in Chicago.Sample Chicago’s 4 favorite food groups – pizza, hot dogs, brownies, and beer. You’ll learn the history behind the iconic foods and also get a taste of some of Chicago’s most popular neighborhoods. On the daytime version of the tour, cruise through Wrigleyville, Gold Coast, Old Town, Lakeview, and Lincoln Park. On the nighttime version of the tour, bike through the skyscrapers and bars of downtown Chicago and see Millennium Park and Buckingham Fountain at night. On either route, enjoy the beautiful lakefront trail as well. This tour is 13 miles with perfect breaks along the way for sampling. Your experienced guide will keep you safe, in-the-know, and well-fed. Bikes provided.

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Chicago: Private 3-Hour Al Capone Gangster Tour

6. Chicago: Private 3-Hour Al Capone Gangster Tour

Experience amazing stories of true crime coming to life on this three-hour private tour. Visit many of the old venues where gangsters used to operate, including old speakeasies and historic hotels. Your expert historian guide will accompany you and your private group in luxury accommodation to historically significant locations in the city. View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, and the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy guns. See the site of the infamous St. Valentine’s Day Massacre, and sit in Al Capone’s booth at the Green Mill. Finally, visit the location where Public Enemy #1 John Dillinger was assassinated by the FBI.

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Chicago: 2.5-Hour Amazing Scavenger Hunt Adventure

7. Chicago: 2.5-Hour Amazing Scavenger Hunt Adventure

Turn downtown Chicago into your own personal giant game board with Urban Adventure Quest, an interactive Amazing Race-style scavenger hunt that allows you to do just that. On this 2.5-hour sightseeing tour of Chicago, you’ll be guided from your smartphone through the city on a fun, team-building journey. This is the perfect tour for groups – large or small – looking to make their way to the most well-known sites, as well as to those often-overlooked hidden gems the city keeps secret. Race to be the first to finish the game, or take as much time as you need, solving clues, completing challenges, and learning about local history along the way. The adventure will start riverside among the historic buildings and will take you along a game route that will show you the rich history, strong focus on public art, and indelible culture of this great city.   Points of interest on your quest: Riverfront Hard Rock The Bean Art Institute of Chicago Palmer House

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The Chicago Theatre Marquee Tour

8. The Chicago Theatre Marquee Tour

Explore the grandeur of The Chicago Theatre, which opened in 1921, on a 1-hour guided tour. Your guide will accompany you through the elegant lobby, sweeping staircase and the majestic auditorium, which is complete with murals above the stage and on the ceiling. During your visit, you will get access to various sections of the seven-story, 3,600-seat auditorium and an intimate view of the 29-rank Wurlitzer theatre pipe organ, the first musical instrument having attained a city landmark status.  Next, view artist signatures on the dressing room walls, including Frank Sinatra, Dean Martin, Dolly Parton and many more. You will finish your tour on a high and feeling like a star as you get the chance to stand on the famous Chicago Theatre stage. Once called “the Wonder Theatre of the World”, the Chicago Theatre hosts over 175 events a year, bringing together the world’s brightest stars and greatest productions.

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Chicago: Downtown Architectural Interiors Tour

9. Chicago: Downtown Architectural Interiors Tour

Jump right into beautiful architectural interiors of the Roaring '20s, taking in the class and elegance of a classic Art Deco masterpiece. Go back 50 years to the 1880s and explore the structure and style of one of the most famous and oldest buildings in downtown Chicago. Next, you'll marvel at a vaulted ceiling from the Postmodern era, surrounded by Moorish details. Finally, you'll end looking up at the world's largest Tiffany stained-glass mosaic, and very close to the world-famous Millennium Park with one of the most famous landmarks of Chicago, "The Bean."

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Xplori 4G SIM Card for US

10. Xplori 4G SIM Card for US

Stay connected while traveling around the US with a 4G sim card from the leading mobile operator in the US, AT&T. Use your sim immediately — no need to register. Make calls to over 100 destinations worldwide for just $0.20/ minute.  Activation procedure: Please ensure that data and data roaming are turned on for your mobile device (for iOS: Settings > Mobile Data and Mobile Data Options; for Android: Settings > Mobile Networks). Wait for a few minutes for your mobile device and sim card to sync, restart your mobile device if this takes too long. If the sim cannot find the network by itself, please select ‘AT&T’ manually.

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

4.5 / 5

based on 30 reviews

Kai was an excellent guide for our activity last night. She had so much knowledge of Chicago history and when we requested more of history/ gangster knowledge vs just the speak easy stops, she made a significant pivot to make our activity specific to our requests. Would highly recommend this tour and Kai!

Gabe made it so fun & interesting. Felt very safe. He was great at navigating around crowds, etc. We plan on repeating this tour with friends!!

Very Informative, tour guide was considerate (in pacing of the walk) for the group, since the majority was over 65.

The tour guide was amazing! We were very happy to meet wonderful people ! We had lots of fun !

Great experience, loved our guide, Gabe! Great way to enjoy a few hours, you won't regret it.