Life is more fun with friends! It’s also more fun when you can cruise around Chicago experiencing the Windy City and all that it has to offer! So, whether you’re looking for a bachelor or bachelorette party idea, an educational and exciting field trip, or something to do after your wine and cheese party – this article is your guide to fun group activities in Chicago!

One: Spend the morning exploring Chicago with the good folks at Bobby’s Bike Hike

Bobby’s Bike Hike tours of Chicago are a wonderful group outing idea for groups ranging in size from 1 to 200, especially during the spring, summer and fall seasons when the city is at its outdoor best. You can take a group of friends or your kids along to enjoy the unique neighborhoods and attractions along a variety of routes. Many of the tours also take you to various eating places along the way where you can sample Chicago staples like deep-dish pizza, hot dogs and craft beer.  These particular Chicago food tours are always popular for groups of adults. Bikes and food samples are included in the fee, as well as child bikes and equipment should you be planning a family reunion or such. No matter the type of group, there’s always a guaranteed fun factor at Bobby’s Bike Hike, and this is an activity in Chicago you should not miss.


Two: Enjoy a dinner boat ride with Entertainment Cruises

Entertainment Cruises provides various fun options for groups of friends for any special occasion. And it could also make a great romantic escape after a fun, summer gathering. Groups of 1-19 can book online while parties of 20+ should contact one of their on-staff event planners. Our personal favorite is the sunset and evening cruises on the Odyssey, which are not to be missed. There are loads of activities onboard the boat which adds to the diversity of options within this choice, including 3-course dinner, dancing, or just taking in the incredible Chicago skyline view.

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Three: Enjoy sketch comedy at Second City

Who doesn’t like to LOL in real life? The skits and comedy at The Second City Chicago will leave you in a laughing fit. For over half a century, The Second City has been daring audiences to laugh at our world, our shared troubles, and ourselves. It’s always fun to take friends along, so it’s a great group outing idea, especially fun for bachelor and bachelorette parties. And the Second City bar sells beer packages, so the bachelor bro factor can be at a level 10.  You can even go alone if you’re feeling low someday to help yourself feel better. Bring your group of 16 or more to enjoy the latest of cutting-edge sketch comedy combined with songs & improv at the world’s greatest comedy theater. Since it’s indoors, you can go any time of year you like.

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Four: Explore the natural wonders of the Field Museum

The Field Museum is the perfect place to visit if you’re planning educational field trips for pre-k, elementary, middle school, all the way up to high school students. Home school students, don’t fret, they have you covered as well.  The Field Museum’s field trip experiences offer exciting, hands-on exposure to social studies and science in a historic Chicago setting. The Field is filled with unique and exciting natural exhibits that would pique every kid’s curiosity. You also get tickets cheaper if you buy them in bulk, which makes it even better an offer for school groups on a tight budget. It’s an educational activity as well, so taking kids there is especially a good idea to stimulate young minds. Because of the indoor abundance of the museum, this activity is great any time of the year, but especially in winter months when it’s always nice to cozy up in their vast setting. Field trips and student programs are available for groups of 15 or more.

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Five: Chicago Magic Lounge

If you’re interested in magic shows, Chicago Magic Lounge is certainly the place you should go to on the weekend in Chicago. They do a blend of close-up and parlor magic and their brand of close-up magic is highly interactive and participatory. Fast, fun and informal, Chicago-style magic doesn’t just break the proverbial 4th wall, it walks over and sits down at your table. You’ll find magic around every corner – from the secret doors to the magicians performing impossible feats right before your very eyes. It’s entertaining and a fun activity for groups of friends because not only do you get to enjoy the show, you can also share cocktails with your friends there. Can somebody say ‘win win’?  It could even make a fun, memorable idea for a birthday celebration.  Going to the Magic Lounge any evening would make for a great night, and magic is nice year-round.  The Magic Lounge can accommodate groups from 4 to 116 (though anything over 80 people would require a buyout of the venue).

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So, what are you waiting for? Get to planning! Send out those e-vites or set up a group chat in WhatsApp, and get your squad together and get to making some memories in Chicago.

Need more ideas? Give us a call anytime at (312) 245-9300 and one of our expert Chicago tour guides can offer advice.