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There are many reasons why Chicago is an epic city for a bachelor party. So if you’re feeling daunted trying to plan the perfect bachelor weekend there, don’t fret. This list of the best things to do will help simplify your plans.

From catching a ball game at the infamous Wrigley Field to enjoying the perfect deep-dish pizza, you can’t go wrong with a trip to the Windy City. The groom-to-be will have his pick of live music, boating adventures, and laidback sporting events. 

The top Chicago bachelor party activities include:

  • Catching a game at Wrigley Field
  • Enjoy stand-up comedy
  • Try axe throwing
  • Attend a music festival
  • Have some beers in Germantown
  • Relax at a bathhouse
  • Hang out in Navy Pier
  • Charter a boat on Lake Michigan
  • Mini golf with a view

Planning a Bachelor Party in Chicago 

And we all know how notoriously hard planning a group trip among guys is. Troupe’s group travel planner takes the annoyance out of planning a bachelor party trip to Chicago. Use the site to let your buddies vote on their favorite options for accommodation, share their flight info, and coordinate activities. Voila! No more annoying, endless texts or email threads.

This big city (like all others) has plenty of nightlife and wonderful eateries, so we’re going to focus more on the fun stuff to do. If you do need restaurant suggestions, Gibson Italia and Maple & Ash are solid options. We have no doubt you’ll be able to find the bars on your own. 

Chicago Bachelor Party Ideas

Catch a game at Wrigley Field 

Grab some beers and hot dogs and enjoy watching the cubs play at the infamous Wrigley Field. If you’re flexible on dates, consider seeing if/when the bachelor’s favorite team might be playing at Wrigley.

shot of the crowd at Wrigley Field. Blurred heads in the stands in the background and 2 guys wearing Cubs gear in the foreground.

Enjoy a comedy show

Ready to share some laughs with your bachelor party crew in Chicago? Head to The Second City in Old Town, the legendary stomping grounds of comedians like Tina Fey and Bill Murray. Many big-name comedians got their starts here. This club was a huge catalyst for the rise in popularity of sketch and improv comedy.

Axe Throwing

Strong man throw axe. Channel your inner caveman (lumberjack?) and practice chucking axes at targets at Bad Axe Throwing. You’ll be able to grab food and beers at the restaurant either before or after your axe throwing extravaganza. 

Music Festivals

If you visit in the summer you’ll have your choice of live music events. Is your groom-to-be a festival junkie? Beloved Lollapalooza, the city’s biggest music festival, could make a great choice for a bachelor party weekend. Even if you don’t make it to one of the big ones, you’re sure to find an outdoor concert while you’re in town during the warm weather. Millennium Park Summer Music Series is a great place to start looking. 

Music festival lovers can also check out our camping festival essentials packing list.

Crowd of screaming fans at an outdoor music festival, one of the best things to do for a bachelor party in Chicago

Have some beers in Lincoln Square (Germantown) 

If the guest of honor has German roots (or even if they don’t) it could be fun to pay a visit to Chicago’s Lincoln Square. This historic German neighborhood boasts cobblestone streets, sausage shops, and beer gardens. 

Relax at a bathhouse 

If the future groom enjoys being pampered, consider spending an afternoon at one of the city’s bathhouses. There is a wide range of spas to choose from in the city, including Turkish-, Russian-, and Korean-inspired venues. Taking some time to relax and unwind makes a great addition to a bachelor party in Chicago.

Mini golf with a view

There’s nothing like a rousing game of mini-golf to get in the bachelor party mood. Head to City Mini Golf in the middle of Maggie Daley Park where you can play 18 holes beneath a magnificent view of the Chicago Skyline. 

Hang out in Navy Pier 

At the beer garden here, you’ll often find free live music and an upbeat atmosphere. Navy Pier is also a great place to leisure away an afternoon. If you and the boys are feeling extra fun, take a ride on the Ferris wheel.

Charter a boat on Lake Michigan

Charter a boat to spend a day on the lake. Toss out anchor and post up at ‘Playpen’. You shouldn’t have trouble finding it. This area of the water turns into a massive boat party every weekend during the summer. 

Where to Stay for a Chicago Bachelor Party

Decide with your group whether you’d rather rent an Airbnb or get a handful of hotel rooms for the bachelor party. If you choose the hotel, The Wit Chicago is an ideal place to stay. Located in the theatre district, just around the corner from The Bean and Magnificient Mile.

This is the perfect hotel in Chicago for a bachelor party because it offers double bedrooms and it’s in the perfect location for all the activities you may want to do. Take the elevator all the way to the top and you’ll find their award-winning rooftop lounge with killer skyline views and world-renowned DJs.

bachelor party in chicago photo of the bean with lots of people

Not sold on a bachelor party in Chicago? What about a bachelor party in Denver? Or enjoy some brewery tours on a Boston bachelor party.

Or, if you’re looking for something further south, check out these tips for a bachelor party in San Diego.

For the future Mrs., discover the ultimate guide to a Napa bachelorette party or check out these bachelorette destinations on a budget.