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The Style Blog

Chicago Bachelor Party Ideas

Written by Diana Ganz November 23, 2019
Wondering where to go on your bachelor party? Not only is Chicago a world class city, rich in history and culture, its central location also makes it a great destination for a group spread coast to coast. Located on Lake Michigan, the city makes the most of its water proximity with multiple beaches to escape the concrete jungle and waterways which course through downtown like an industrial Venice. Off the lake, it serves up every scene imaginable with a never-ending list of neighborhood bars and restaurants without a last call if you know where to go. With so much to offer, you and your guys will be blown away by the bachelor party you plan in the Windy City.
One important consideration when planning a bachelor party in Chicago is that not all seasons have a special appeal and, in this case, that season is winter. We’ll be frank here, there is nothing appealing about visiting Chicago during the winter. There are no mountains to head to. It’s not particularly sunny. The only exception being St. Patrick’s Day. Throwing your bachelor party St. Patrick’s Day weekend will not disappoint. Chicago goes all out and even turns their river bright green. It’s one of those life bucket list activities you and your guys will remember for a while.
There so much to do in Chicago that choosing exactly what you want to do might be your biggest challenge. Here’s our list of ideas for a bachelor party in Chicago:
Get On The Water
307 miles long and 118 miles wide, Lake Michigan feels like an ocean and is a hotspot for all types of activities from fishing to nationally ranked city tours. Known for great salmon and trout fishing, you can charter a fishing trip for 5 hours to 2 days. Everyone will need a fishing license, but that can be arranged online and purchased for only one day.
Looking for more leisure and a little less work? Rent a private boat for the day and head out to the Playpen, Chicago’s floating daytime club scene where boats raft up, play music and people are making the most of their summer in Chicago. You are sure to make some friends and great memories at that lake hotspot!
If your group appreciates history and architecture, you must check out Chicago’s Architecture Boat Tour. Rated one of the top tours in the US, you will be blow away by all the history and famous architecture the city holds. This is hands down one of the best things to do in Chicago and recommended by most locals. Even if you don’t feel like channeling your inner Frank-Lloyd Wright, you and your friends can take advantage of the onboard full-service bar while you cruise through downtown basking in the sun.  
Sports Fix
Want to plan a sport centric bachelor party weekend? Chicagoans are crazy about their sports teams and all the pageantry that comes with. One game can literally consume an entire day with pre and post party events reminiscent of your college tailgate days. The second oldest ball park in America, Wrigley Field is home to the Cubs, 2016 World Series Champs, and nestled in one of Chicago’s most happening neighborhoods. Depending on the time of year you visit, you can catch a Bulls and Cubs game or a Bears, Cubs and Blackhawks game all in one long weekend! 
Big Ten fan? Every year Chicago host the Big Ten Championships in early March and sometimes that coincides with St. Patrick’s Day weekend in the city which is double the fun!
Game Rooms
If your group prefers to participate rather than be spectators, Chicago offers some really great gaming adventures for a bachelor party weekend. If you’re looking for some 16-bit nostalgia coupled with craft beers or just love a good pinball machine, check out one of the three Emporium arcade bars. Hidden in the Chicago Athletic Association, you will find their Game Room offering all the classics like bocce, shuffle board, billiards, foosball and more with plenty of flat-screen TVs so you can watch your team compete while you do the same against your friends. Additionally, all the games at the CAA are free, but their exceptional cocktails you’ll have to pay for. The CAA also features two amazing restaurants (The Cherry Circle Room and Cindy’s Rooftop) and a posh, speak-easy style 8 seat cocktail bar called the Milk Room for which reservations must be made at least a month or two in advance. They specialize in drinks made with rare vintage spirits and elixirs mostly bought at auctions and often the last of their kind
If you want to get a little more physical, you can checkout Whirlyball just north of downtown. Enjoy a beer while you battle it out in Whirlyball, a combination of lacrosse, hockey, basketball and bumper cars! This facility also features laser tag and bowling and is a hot spot for bachelor parties looking for a fun afternoon activity. Nothing says a guys weekend like a little friendly competition.
Incidentally, The Groomsman Suit is across the street from Whirlyball making it even more of a destination spot for bachelor parties. Before you embark on a night of fun, bring the group in to get fitted for their wedding suits. You can enjoy a beer on us and check a major thing off your wedding planning to-do list! You can schedule an appointment for your group here.
Foodie Paradise
Chicago’s good scene is more than hot dogs and deep dish, although, those are important food groups on your bachelor party weekend. Almost anywhere and anytime, you can hit up one of over 2000 hotdog trucks throughout the city. Going for deep dish, however, takes a little more planning as those thick pies take a minute (or 60) to bake. Our deep-dish recommendations include Pequods, Giordano’s, Lou Malnati’s, and the lesser known Art of Pizza.
Of course, it’s best to even things out with some fine dining and Chicago is packed with some of the best high-end restaurants in the US. Start your night out with some fancy cocktails at the Aviary or the Milk Room. From there you can indulge in just about any type of cuisine. Being in the Midwest, Chicago has some pretty incredible steakhouses that will serve up a memorable meal. Word of caution, Chicago restaurants are not afraid of rare red meat. If you typically order your steak medium rare, you might want to ask for medium. Medium rare in Chicago is rare by most other cities’ standards. Three of our favorite steakhouses are RPM Steak, El Che and Maple & Ash.
If you’re looking for something a little more exotic, head to the West Loop. There you can find Chicago favorites like Girl & the Goat (tastiest small plates), Avec (Mediterranean), Monteverde (Italian) and many others. For a fresh list of Chicago’s best restaurants, check out TimeOut’s list of 48 restaurants you must try.
Beer Town USA
With over 160 breweries, Chicago has more breweries than any other city in the US. Hometown favorites include Goose Island, Revolution Brewing, Half Acre, and Lagunitas. For a complete list, check out The Hop Review’s Comprehensive Brewery List of Chicago. Can’t decide which one’s to try, schedule a brewery tour and let someone else plan the itinerary. Cheers!
Live Shows
From festival weekends to local neighborhood clubs, you can find whatever genre you’re into. Chicago is a must stop for major musical acts large and small and home to some of the country’s largest summer musical festivals like Lallapalooza and Pitchfork. The Hideout, Shubas or Kingston Mines are popular late-night spots that always have something going on.
Home to the famous Second City comedy club, comedy is in Chicago’s blood. Every night of the week you’ll find improv and stand up shows featuring some of the country’s most talented comedians. This might be the perfect thing to head to after that brewery tour!
Endearingly nicknamed the City of Broad Shoulders (for its incredible diversity and abundance of food and drink), Chicago has something for every type of bachelor party - it’s rich in history and architecture, steeped in sports culture, a pioneer of the modern cocktail revival and boasts 25 Michelin star restaurants. Good luck and feel free to contact us if you need any more recommendations on suiting or the city! After all , it’s our hometown and where we are headquartered!
Planning a bachelor party elsewhere or just getting the planning process started? Check out our guide for Bachelor Party Ideas to help you create a memorable trip!


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About the Author

Diana Ganz - The Groomsman Suit

Diana Ganz is the co-founder of The Groomsman Suit. Being a passionate advocate for the TGS brand, Diana oversees marketing and branding efforts to bring maximum visibility and growth. She enjoys building relationships with engaged couples and industry partners and is committed to creating a fun, easy and thrilling purchasing experience for all TGS customers.

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