A Chicago Bachelor Party City Guide to Plan Your Weekend

If you're searching for the ultimate bachelor party spot, look no further than the Windy City. The Midwestern destination has so much to do: boating, sports events, bar hopping, food tours, live music, museums and more. If you're thinking of planning a Chicago bachelor party but don't know where to begin, we've got you covered. Rather than scrolling through the bachelor party Chicago thread on Reddit, check out our guide instead. With everything from party ideas for every personality to a packed three-day itinerary to lodging recommendations, we'll help you plan the ultimate Chicago bachelor party for your guest of honor.

What Are Some Chicago Bachelor Party Ideas?

Chicago offers all the big city attractions—rooftop bars, sports events, award-winning restaurants, arts and culture—as well as boating or beaching. Check out these fun Chicago bachelor party ideas below.

For the Sports Fans

Is your guest of honor into sports? There are a ton of opportunities for you and your crew to get rowdy at a game in Chicago. Choose from a Blackhawks hockey game, a Cubs or Sox baseball game, a Bulls basketball game or a Bears football game (plus so many other sporting events). Plan a tailgate for your group and get matching apparel to commemorate the experience.

For the Foodies

Tell your crew to bring their appetite to the Windy City. Chicago is known for so many delicious foods like deep dish pizza, hot dogs and Italian beef. Grab a slice, taste the city's famous popcorn, buy a dozen old-fashioned doughnuts or try some world-class barbecue. Plan a tour and check out all the amazing restaurants and food stands in the city with your crew for an unforgettable, food-filled weekend.

For the Water Lovers

What could be better than boating with your best friends? Book seats on the famous architecture tour or rent your own electric boat. If you're looking for a boating party scene, drive over to Playpen, a breakwall-protected area on Lake Michigan that boasts impressive views of the surrounding skyline. Since Chicago is located on Lake Michigan, there are also two beaches your crew can enjoy: North Avenue Beach and Oak Street Beach. Lay out on the sand, play volleyball (or spikeball) and enjoy snacks from the nearby shacks.

For the Party People

When it comes to bars, Chicago has it all. If you like live music, there are country bars, blues clubs and alternative music venues all over the city. If you're more into sports bars, check out the assortment of places up in Wrigleyville, the different Bears-themed spots near Soldier field or the official Blackhawks bars. Pop into game-themed bars to play darts, ping pong or arcade classics. Or, take in views of the city from the various rooftop bars like London House, Cindy's or The J. Parker. All of these options are easily accessible by the L, the city's above-ground train system. Looking for something more interactive? Book a brewery tour or a trolley bar crawl—or check out popular craft cocktail spots.

For the Golfers

Tee off at Sydney Marovitz Golf Course, a lakefront public course where you can golf next to stunning panoramic views. There are plenty of other golf courses in the city to choose from, but this one is right on Lake Michigan.

For the Culture Enthusiasts

If your crew (or guest of honor) is on the artsy side, there's plenty to check out in the Windy City. Take a trip to the Art Institute of Chicago, one of the oldest and largest museums in the United States. Beyond museums, Chicago offers a wealth of different arts. Enjoy the live music scene, the Chicago Symphony Orchestra, the murals around the city or The House of Blues.

What Do You Do at a Bachelor Party in Chicago?

Not sure how to narrow down all of the options available? We created a three-day itinerary for a Chicago bachelor party filled with food, drinks and fun.

Day 1

Morning: Check into your hotel or rental space and fuel up with brunch at ZED451 in River North. Get an all-inclusive meal featuring breakfast staples (eggs, french toast, biscuits and gravy, bacon and pastries). Once you've loaded up your plates, enjoy the brazilian steakhouse vibe, where servers slice different meats tableside. Don't forget to order a cocktail like the popular sriracha ranch bloody mary. Once you're finished, take the train uptown to Wrigleyville.

Afternoon: Wrigleyville is the location of Wrigley Field (home to the famed Chicago Cubs). If it's baseball season, get your group tickets to see the team play and enjoy an afternoon in the sun (load up on beers, nachos, hot dogs—the works). If the team isn't playing, enjoy the local sporty scene by bar hopping (check out Old Crow Smokehouse, Big Star and Sluggers) and picking up a famous Chicago-style hot dog.

Evening: Enjoy dinner at Au Cheval, a famous upscale burger joint (just prepare yourself for a wait). Pro tip: put your name in early and check out Punch Bowl Social (a bar full of games and shareable drinks) in the meantime. For dessert, get scoops from Jeni's Splendid Ice Creams. Later, grab a cocktail at Apogee or head to the party scene at ROOF on the Wit. Feel like clubbing? Check out DISCO or Tao (both located in River North) or PRYSM Nightclub (situated in Lincoln Park). If you're still hungry, pick up a late-night snack from Al's Italian Beef.

Day 2

Morning: Head over to Lincoln Park for brunch at Batter and Berries. This hotspot tends to be busy, so expect a wait. Pick up some beverages for your crew (the restaurant is BYOB) to pass the time and enjoy dishes like the French toast flight (complete with strawberry, blueberry, lemon and caramel french toast) or the cluck-n-gaufre, a sweet potato waffle stuffed and topped with fried chicken and hot sauce.

Afternoon: Take advantage of Chicago River and Lake Michigan. Rent an electric boat (it's cheaper than it sounds, BYOB and just like driving a golf cart) and cruise around the river. Looking for a party scene on the water? Head over to the Playpen, an enclave off of Oak Street Beach for boaters. When you're done, head over to the beach to play volleyball or spikeball. On your way there, stop at Navy Pier and ride the iconic ferris wheel.

Evening: Grab drinks at Cindy's, a popular cocktail rooftop and take in the sunset and the lake. Then, head to Logan Square for dinner at Longman & Eagle. The Slagel burger with Widmer's cheddar (both Midwestern companies) and beef fat fries are a popular choice. You can also try their other delicious dishes like cornish hen pot pie and wild boar sloppy joes. Stick around Logan Square to check out the Milwaukee Avenue corridor. Hop into Empty Bottle and The Hideout to see everything from up-and-coming indie rock bands to live comedy. Then head over to Emporium to enjoy arcade games, dozens of beers and 60-plus whiskeys in a loft-like setting. Grab drinks at Revolution Brew Pub, one of Chicago's leading craft breweries and then head to Cole's Bar and East Room (both dive bars with a fun party scene). End your night at Slippery Slope playing Skee-ball and dancing. If you want to go clubbing afterwards, check out Smart Bar in Wrigleyville, Danny's Tavern in Bucktown or The Underground in River North.

Day 3

Morning: Enjoy brunch on the Chicago River at River Roast. They serve classic dishes like breakfast hash, chicken and waffles (of course) and french toast. But they also offer other unique options like charcuterie boards, oysters and roasts that are hand-carved tableside.

Afternoon: Tee up at Sydney Marovitz, an affordable public course on Lake Michigan where you can golf next to stunning panoramic views. When you're done, head to Millennium Park, where you'll find the iconic bean and the 606 trail (modeled after NYC's High Line). Keep exploring the park or pop into the Art Institute of Chicago to see the extensive collection of artwork. Check out the fun restaurants in the area, like the Nutella Cafe, Garrett Popcorn or Velvet Taco. Feel like hitting up a day party? Head over to Federales in the West Loop for margaritas and tequila shots served in an ice glass (which you can throw at their oversize bell).

Evening: Get dinner at Broken English Taco Pub, which combines a unique take on Mexican street style tacos, refreshing beverages, eclectic music, and vivid artwork created by local talent. Afterwards, go see an improv show at The Second City, the company where comedians like Tina Fey, Steve Carell and Amy Poehler got their start. If you still have energy and are looking for a more club-like vibe, make your way to The VIG or head uptown to Beaumont Bar & Grill for late-night dancing.

Where Should I Stay in Chicago for a Bachelor Party?

There are plenty of housing options for a Chicago bachelor party, so check out TripAdvisor, Airbnb and Vrbo for top recommendations. To help, we rounded up a few great places to stay while you party in the Windy City.

Best Chicago Bachelor Party Hotels

ACME Hotel: A downtown spot complete with its own mixology den (Berkshire Room) and an apres ski party bar (Bunny Slope) that you can rent out for you and your crew. They've also got in-suite guitars, in-room beer vending machines, free Apple watches to check out during your stay, and hangover kits as part of their "Hair of the Dog" package.

The Drake: One of Chicago's most historic hotels located in the beautiful Gold Coast area. It offers sweeping lake views, a gym and three restaurants.

Chicago Athletic Association: Newly renovated and located in River North, the CAA has luxe rooms, a restaurant, a Shake Shack (yes, really), a game room and Cindy's, a popular rooftop bar.

Best Chicago Bachelor Party Airbnbs

Small Groups: Stay this spacious three-bedroom loft space, complete with a pool table, a screening room with surround sound and a chef's kitchen.

Medium Groups: Consider a stylish three-bedroom loft in Wicker Park for your group. It has breathtaking views and plenty of common space everyone to hang out in.

Large Groups: Book a three-level penthouse for your group. This one is situated in West Town (just below Wicker Park) and fits more than 14 people, so you'll have plenty of room. Psst: it has a private rooftop deck too.