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12 Insanely Fun Group Activities in Chicago for 2021

Chicago is a vibrant, lively city with a rich and colorful history. Cleaner than New York, and with a richer, and more complex history than LA, it’s easy to fall in love with the wide variety of recreational activities and things to do and see in the windy city. If you’re looking for the best group activities that your family and friends will love, Chicago has no shortage of incredibly exciting, stimulating, and engaging things to do! 

The Vibrant Streets of Chicago

Start planning your next day out with this list of specially selected 12 insanely fun activities, chosen especially for large groups. 


1. Tickle Your Tastebuds With Sidewalk Food Tours Chicago Walking Tour

Sidewalk Food Tours Chicago Walking Tour. a plate of food on a table

Chicago is known for so many iconic dishes and foods, from deep-dish Chicago-style pizza to authentic tapas and the best American donuts available in the country! You and your group can have the chance to experience all these and more with the Sidewalk Food Tours Chicago Walking Tour. 



2. Get an Incredible Adrenaline Rush at iFLY Lincoln Park

Team Building Indoor Sky Diving. Two people sky diving

If you’re looking to create incredible memories, and build a strong connection amongst your group, indoor skydiving is one of the most exhilarating group activities out there in Chicago! The thrills and excitements can instantly bond you and your group. iFLY offers birthday parties, team-building events, and many more booking options, so speak to a member of the team to book your perfect experience today. 

3. Get Competitive at Game Night Out

Get Competitive with a Board Game

If your group is keen on competition, Game Night Out is a perfect group activity for you. It’s just like having a game night in at your home, but you can leave the hosting aspect to the experts! Each group experience is 100% unique and curated, so you can be sure to have a night with something for everyone, no matter your group’s different personalities, tastes, and gaming preferences. 

4. Practice Your Ping-Pong Skills at SPiN Chicago

Play a rousing game of Ping Pong with your friends

Sometimes a friendly game of ping-pong, some beer, and good food is all you need to create a memorable group experience. Take your ping-pong experience to the next level by making a booking with SPiN Chicago. Bookings include catering packages, so your group can stay focused on the game and enjoy the night! 

5. Get Your Culture Fix at the Art Institute of Chicago

a painting of a man and a woman posing for a photo

If you’re looking to take in some masterpieces and have an awe-inspiring group experience, the Art Institute of Chicago is home to over 30,000 artworks from all across the globe. Entry to the museum is low-cost, making it a fantastic, affordable day out your group will love.


6. Take in the Cityscape at 360 Chicago

Take in Chicago's Stunning City Scape

If you’re not afraid of heights and looking to see Chicago as you’ve never seen it before, 360 Chicago offers amazing views of the entire city 1030 feet above the iconic cityscape. Enjoy a cocktail at the bar with your group, or experience some of the interactive exhibits and learn more about one of America’s most iconic cities. 

The star attraction is TILT, which allows you and your group to experience a glass-enclosed platform that tilts over the city at an angle of 30 degrees. The most thrill-seeking groups will love the chance to see Chicago in an up-close and adrenaline-fuelled way. 

7. Get Your Chef’s Hat On at Chicago Dine-Around

Great Chicago Cooking Classes

If you want to take your passion for food to the next level, look no further than the incredible culinary team-building experience on offer at Chicago Dine-Around. Teams complete and compete in hands-on activities, learning recipes and cooking methods as they prepare their very own delectable meal. 

Packages are available for a minimum of 12 guests. Get in touch and book today for an insanely fun night to remember!


8. Marvel at Zoo Animals for Free at Lincoln Park Zoo

Cute Animals at Chicago's free Lincoln Park Zoo

Lincoln Park Zoo is one of the few free zoos remaining in America. With more than 1,000 different animals from around the world, you can enjoy an unforgettable day out on a budget. There’s something for every animal-lover to see, so book your ticket today. 


9. Put Your Escape Skills to the Test at Fox in a Box

Team Building activities like escape rooms are all the rage in Chicago

If you want to grow closer as a group, and improve your teamwork skills, an escape room is a fantastic way to do so! Push your problem-solving skills to the limit in equally fun and challenging escape room scenarios. 

There are four unique and exciting escape rooms to choose from. Rooms host up to 25 people, so bring all your friends along for a thrilling and memorable day out. 

10. Enjoy a Free Drive-In Movie at Rock Island Public House

Enjoy a Free Drive-In Movie in Chicago

Get back to basics and have an affordable night-out together in the comfort of your car, with a free drive-in movie at Rock Island Public House. Parking spots are first-come-first-served, and available every Friday, Saturday, and Sunday night. Food and drink are also available, allowing you to make an evening of it with your group. 

No matter your tastes, there’s something on to suit everyone, so check out the schedule today. 

11. Take Part in an Incredible Scavenger Hunt at CityHunt Chicago

A map. A Chicago Scavenger Hunt is always fun

You can practice your teamwork, and strengthen your bond with CityHunt Chicago. This incredible group experience allows you to have a range of interactive adventures together, and explore and get to know Chicago. With role-play and tour activities within the scavenger hunt, you can come away from the night with hilarious pictures and unforgettable memories. Fill out a form online to book today. 

12. Marvel at Real-Life Magic at The Magic Penthouse

Marvel at real life amazing magic

If your group is looking for jaw-dropping entertainment over cocktails, the Magic Penthouse offers the best magician-themed night out in Chicago. Get up close and personal with real magic, with tricks involving only a deck of cards, your phone, or your wallet. You’ll be wondering the secrets behind the acts long after the final performance!