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13 Insanely Fun Group Activities in Chicago

Published by Josh Hirsch.

Chicago is a landmark of American culture and one of America’s most iconic cities. The good thing about the city is everyone has a different reason as to why they love it. This should be enough to tell you why Chicago is one of the more lovable and iconic cities in the world. From its beautiful beaches, frequent visits from the notorious prisoner Al Capone, being blown away by Windy City with its breathtaking skyline views and beautiful buildings, Chicago has everything you want in a city and has so much more to offer. Oh, did we mention the pleasure of tasting the world-renowned deep-dish pizza?

Chicago is attractive, entertaining and cultural all at the same time. We’ve picked out 13 insanely fun group activities that will allow you to experience the true beauty of all of Chicago. 

pepperoni pizza

You’ve heard the rumors, now try the real thing

Take a tour with glorious food and enjoy the different cuisines with Sidewalk Tours. If you’re a food lover, this one you certainly cannot miss. Fill your stomach with tasty dishes that will want to make you come for more!

Sit back with a cocktail and enjoy the company of professional magicians at the Magic Penthouse. Experience up-close magic and prepare to be blown away by the illusional skills and acts. Be wary if the magicians that ask you for a prized possession, such as cards, phones and wallets as they could disappear forever! Jokes aside, enjoy a unique magic experience that has never disappointed locals over the years.

Sign outside the Movieland Theater

They don’t make theaters like this one anymore

The Chicagoland Theater delivers an experience an atmosphere that can only be considered as vibrant and lively. It’s not just a normal theater center, it’s a rented space so you can enjoy an eventful time with the group whilst choosing from watching big-budget blockbusters, Hollywood classics or an indie flick.

  • Unleash Your Golf Skills at Topgolf 

These days, golf is considered a fun pastime enjoyed with multiple people. Not just that, the Topgolf course isn’t just the home for teeing off, it is also a premier entertainment destination where you can enjoy parties, date nights, formal events or just a quiet night out with friends with a cocktail or two. Enjoy some sprawling entertainment value with or without a golf club.

an indoor skydiving tunnel

Experience all of the thrill without any of the danger

  • Experience the Thrill of Heights with Indoor Skydiving at iFLY

Feel the thrill and excitement of skydiving. At iFLY Lincoln Park, experience the exhilaration of indoor skydiving, the next closest experience to the real thing outdoors. Get your group together, pair up and experience the thrill together. 

Show off your cooking skills with a culinary team-building experience at a hands-on meal preparation class. Learn about different recipe methods, prepare and taste meals and you can even go up a level and compete with others in the class if you’re confident. Enjoy the relaxed atmosphere with a great vibe whilst testing your hand at making delicious meals!

Are you ready to experience an intense game that requires putting your problem-solving skills to the test? The Escape Room is not only intense, but it’s also a lot of fun! Use your intuition to escape from a trapped room and work together within your group to find your way out as fast as you can. Not only is the challenge enjoyable, embrace a closer bond with your group by saving each other from zombies!

a river boat

Take in the views of Chicago from a new perspective

Entertainment cruises fit any special occasion. For a romantic escape, a group night out, a sing-along or a group dinner, there are so many activities you can participate in on a cruise. Enjoy a dance amongst consuming delicious food, overseeing the incredible skyline views. There is nothing better than relaxing on a cruise overseeing the night lights.

actors on stage standing around a table

Get ready to laugh!

Laughter is the best medicine, and the Second City Chicago skit and comedy shows will leave you laughing and smiling throughout. The Second City is well renowned for making audiences laugh until their jaw muscles can’t take it anymore. Enjoy cutting-edge comedy in a vibrant atmosphere whilst topping up your drinks at the bar. 

Take in the exhilarating skyline views whilst enjoying an alcoholic beverage or two at happy hour. Chicago is full of rooftop bars and there is nothing like enjoying a beverage with your group in a vibrant atmosphere on a sunny day. There is always something special at happy hour, and you’re guaranteed to be amongst a large group of people who also just want a good time. It is particularly worthwhile taking up happy hour after a tough hard slog in the office to relax and destress.

two people throwing axes


Axe throwing activity is a great stress reliever particularly if you enjoy a physical encounter. No, not against another human, but a wall. Axe throwing gives you the thrills of a supervised challenge to contest your team members for the highest number of points by throwing an axe at a round target. You can throw in a winner’s prize to make it even more interesting. Bring your food and drink and test your throwing skills.

Get your detective thinking cap on to answer tricky questions with a fun-filled scavenger hunt. Tour and take in Windy City with murder mystery hunts with your team. Test your problem-solving skills and become a champion in solving mysteries. Inspire your friends to take on the challenge and be part of a winning team!

two people playing ping pong

Looking for a competitive edge?

  • Compete in a Game Of Ping Pong at AceBounce

Why not fuel your competitive side with a game or two of ping pong at AceBounce? You can even book a Chicago ping-pong party with a DJ, entertainment, vibrant music and reserve your own cocktail bar for private hire. Fuel your competitive edge with an endless number of drinks to make it a night to remember.


Final Thoughts…

Are you ready to take Chicago by storm? There is no reason to ever become bored in the city. No matter whether you’re looking for fun activities, nightlife, culture, entertainment and dining, Chicago has you covered. Fall in love with one of the most cultural cities in America.