The Complete Chicago Bachelor Party Guide

Take over the Windy City with our itinerary, which includes top rental and nightlife options.
Chicago bachelor party skyline at night city
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james wong - the knot contributing writer and travel expert
James Wong
james wong - the knot contributing writer and travel expert
James Wong
Travel Writer & Expert
  • James Wong is a freelance travel writer and expert.
  • He's reported for publications including VOGUE, GQ, Time Out and Thrillist.
  • James has lived in London, Tokyo and New York; and has traveled to almost every corner of the world.
Updated Feb 09, 2024
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If you're searching for the ultimate bachelor party spot, look no further than the Windy City. The popular Midwestern destination offers much for groups, including boating, sporting events, bar hopping, fine dining, and much more. For that reason, it might even feel overwhelming at first. If you're planning a Chicago bachelor party but don't know where to begin, here's our guide for what to do, where to stay, reservations to book, and places to go. 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 itinerary for your guest of honor.

Chicago Bachelor Party Planning in This Article:

What Are Some Chicago Bachelor Party Ideas?

north avenue beach chicago illinois image of the lake michigan
Pawel Gaul / Getty Images

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

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 aboard GetYourGuide's guided architecture cruise, or rent your own electric boat with Chicago Electric Boat Rentals. 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 spike ball), and enjoy snacks from the nearby shacks.

For the Party People

Chicago has it all when it comes to bars. 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?

chicago city aerial view wrigley field and lake waterfront
franckreporter / Getty Images

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 The Publican in Fulton Market. A chance for the boys to get to know each other within a spacious European-style beer hall, new friends will tuck into farm-fresh poached eggs, sticky waffles, French toast, and big mimosas, all sure to make y'all forget calorie counting for the weekend to come.

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 and start the party 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, Al's Italian Beef is where to pick up a late-night snack.

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 delights 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 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, but if you want to go clubbing afterward, check out Smart Bar in Wrigleyville 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 oversized 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 for dancing and fancy a more club-like vibe, then try The VIG.

Where Should I Stay in Chicago for a Bachelor Party?

TheWit - A Hilton Hotel lobby marble desk and granular columns with funky designs
TheWit - A Hilton Hotel

We've rounded up some great places to stay while you party in the Windy City including a variety of hotels and vacation rentals.

Best Chicago Bachelor Party Hotels

TheWit - A Hilton Hotel rooms looking out to chicago city
TheWit - A Hilton Hotel

Hotel Zachary: There's no better place to be based during game season. Literally across the street from Wrigley Field (they even share an outdoor plaza area), this stylish boutique hotel is both practical and luxurious.

TheWit: This Hilton Hotel is located in Chicago's Loop neighborhood, straddling the shopping, business and theater districts. Recently renovated, what makes it especially worthy for bachelor parties is that it's known for its dining and nightlife scene. All you have to do is head straight to bed after an evening of revelry.

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.

Pro tip: The Knot has partnered with Hotel Planner to help you secure the best group hotel rate and get free hotel advice from an expert travel planner.

Best Chicago Bachelor Party Airbnbs

There are plenty of housing options for a Chicago bachelor party, so check out the best vacation rental sites like Vrbo and Airbnb. Pro tip: If you're looking to supplement your vacation rental stay with some hotel amenities such as a swimming pool or a fitness facility, you can secure Chicago hotel day passes on ResortPass.

Downtown Giraffe Chandelier Loft (Downtown):: This chic loft, perfect for a bachelor party of up to eight, boasts style and convenience at an affordable price. Located minutes from Millennium Park and the Art Institute of Chicago, it offers the excitement and convenience of a central location for an exciting stay.

Aloha Bangtel Tropical Penthouse (Wicker Park): With an average rate of $600 per night, this Wicker Park penthouse is Ideal for sizable bachelor parties. It can comfortably accommodate up to 14 guests, offering ample space for an unforgettable celebration in the heart of the city.

Stylish Four-Bedroom Mid-Century Home (Northwest Side): This stylish Chicago stay, which can sleep up to 15 guests, boasts four bedrooms, three bathrooms, a games room, a patio and a fire pit. Situated a 20-minute drive from downtown, it offers a convenient base for bachelor parties looking to explore the city. There's lots to see and do nearby, too.

Magnificent Mile Penthouse (Downtown Chicago): If you're planning a small bachelor party in Chicago, this penthouse suite can sleep up to four guests. With floor-to-ceiling windows, you'll have the best views of the city during your stay. Trust. On average, this property starts at around $270 per night, pending seasonality.

Artist Loft Duplex in a 1904 Former Factory (River West): Smaller groups should consider this space, complete with a pool table, a screening room with surround sound, and a chef's kitchen.

Historic Apartment (Wicker Park): Groups should consider this exposed brick apartment in Wicker Park. It has breathtaking views and plenty of common space for everyone to hang out.

Three-Level Penthouse (River West): If your group is larger, opt for a rental like this 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.

Chicago Bachelor Party Nightlife

TheWit - A Hilton Hotel rooftop nightlife during day and night
TheWit - A Hilton Hotel

There's a good reason why foodies choose Chicago, and bachelors will want to get a load of hotspots as seen on The Bear. As for drinking, you'll have a splash everywhere from immersive cocktail bars to historic jazz clubs.

Best Chicago Bachelor Restaurants

Gordon Ramsay Burger: Arguably the most recognized chef in the world, Gordon Ramsay is known for so much more than television; in fact, the chef is renowned for excellence in dining no matter the tier. His burger restaurant is a smart yet casual joint for gents to loosen their top buttons and feast on meats cooked just right. That's on big juicy burgers, hot dogs and fried wings, and sides like onion rings and truffle fries, so tasty they could easily serve as a main.

Lao Peng You: Opened by half-brothers in 2019, Lao Peng You is a Chicago sensation when it comes to dumplings. Pork and chive, mushroom and chive, beef and green onion…whatever your filling, you'll want seconds. The restaurant's icon status was further cemented thanks to a starring role in Hulu's The Bear. BYOB makes the slurping extra fun and affordable.

Little Goat Diner: Who says that breakfast is just for breakfast? At Little Goat Diner, you and the gang can enjoy pancakes and corned beef hash up until the evening hours. It's the perfect hangover cure after the most debaucherous of nights. Don't miss the establishment's Grown Up Cold Brew—made with homemade bourbon and sweet cream.

Best Chicago Bachelor Party Bars

Guinness Open Gate Brewery: Chicago's geared up for the hotly anticipated opening of Guinness Open Gate Brewery, which opened in summer 2023. Located in the heart of West Loop, a popular nightlife destination, groups will discover a whole other side to Guinness. With over a dozen rotating beers from the brewer and special imports direct from Ireland, the huge 15,000-square-foot space also includes a full-service restaurant and a bakery. Cheers to that.

The Cauldron: A touch of magic will make this bash one to remember. The Cauldron is a wizard-themed restaurant and bar, housed in a former bank in Wicker Park. Sign the boys up for an immersive cocktail class, where you'll don a cloak and in a science-style class, mix and brew your own drinkable elixirs. The team is well-equipped to host large stag dos, so get in touch here to make a booking.

Kingston Mines Blues Club: The largest and oldest continually operating blues club in Chicago, Kingston Mines is a must for an evening of live music and classic beverages. Bands perform until the early hours every night of the week across two separate stages. This historic venue has hosted blues legends including Koko Taylor and Magic Slim.

Expert Chicago Travel Tips

O'Hare International Airport is well-serviced by airlines across the country, but as Chicago is where United Airlines is based, you're wise to select one of their routes for the biggest flight selection and preferential timings. It's also one of the US airports to boast a Polaris Lounge.

Chicago has one of the best public transport systems in America, so there's no need to rent a car. From the airport, simply take the Blue Line all the way into town. CTA (Chicago Transit Authority) operates buses and trains throughout the city, much like the MTA in New York City. You can purchase a CTA card from train stations and convenience stores. Visit Choose Chicago for full getting-around information. For the best weather, visit April to June, and September to November. Outside of those times though, you'll take advantage of great prices, and Christmas is extra festive in deep snow (we've all seen Home Alone).

Brittany Barber and Maddy Sims contributed to this article.

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