As the unofficial capital of the Midwest, Chicago has a little something for everybody. Sports, sites, and impressive skylines are only the beginning, which is why a Chicago bachelor party has become a go-to location of choice. Treat the whole crew with a visit to Wrigley Field, or spend an afternoon rowing down the Chicago River. In between excursions you’ll want to fuel up on quality beer and deep dish pizza—both of which are in high supply throughout the city.
If urban adventures fall within your group’s travel style, rest assured that a Chicago bachelor party is just the ticket.
What to Do
Newcomers to the Windy City will want to spend their first day exploring the sites that make Chicago a world-class destination. Highlights like Millennium Park, Navy Pier, and the Magnificent Mile only scratch the surface but will give your crew a solid day of sightseeing. For awesome 360 degree views of the city, don’t forget to stop by Skydeck Chicago located on the 103rd floor of Willis Tower. If you’re not intimidated by heights, take it one step further with “The Ledge.” This famous glass balcony extends four feet outside the building, giving you a straight-down street view of 1,353 feet below.
Whether or not you call yourself a Cubs fan, no Chicago trip is complete without a visit to Wrigley Field. Grab tickets to a game, tour the ballpark (or both), and make sure to also enjoy some nightlife in the Wrigleyville neighborhood—filled with sports bars, restaurants, music venues, comedy clubs, and more. Of course, if your Chicago bachelor party falls over football season, cheering on the Bears at Soldier Field is an equally fun way to celebrate the groom-to-be.
During the warm weather months, Chicago’s Lake Michigan shoreline is the place to be. You can run, bike, or skate down the Lakefront Trail, take up a game of volleyball on the beach, go paddle boarding with hourly rentals, or even book a Beer & BBQ Cruise for an evening out on the water. You can also make your way down the Chicago River with rowing, canoeing, and kayaking options that provide a city tour and outdoor adventure all in one.
Chicago has its share of unique breweries and distilleries to explore, and the Chicago Beer Experience and The Barrel Run are two great ways to sip and sample the best of the best. Got a large group to accommodate? Book a private tour for a customized experience everyone will love. If you prefer to a party boat to a party bus, check out Chicago TikiBoat for a unique way to take your drinking shenanigans on the open water.
Where to Eat
Deep dish pizza is a Chicago food staple, so make it a mission to taste test your way to the ultimate slice. Giordano’s, Pequod’s Pizza, and Lou Malnati’s Pizzeria are ranked among the best, but you can’t go wrong sampling pretty much any local pizzeria in the city.
It’s not very often you’ll find a Michelin-star restaurant at an approachable price point, but Longman & Eagle is exactly that. You’ll feast on farm-to-table cuisine and expertly crafted cocktails in an atmosphere that’s both laid-back and decidedly hip. Longman & Eagle also houses a six-room inn above the restaurant so you can dine, drink, and stay all under one roof.
Every Chicago bachelor party should include a steakhouse dinner, and you’ll find plenty of options tucked within this urban hub. Over in River North, Bavette’s Bar & Boeuf takes the fuss out of fine dining with flavorful steaks and seafood served in a vintage club-style setting. For more French-German fusion, check out BoeufHaus in West Town where you’ll find a menu any carnivore would love.
Dubbed “the best dive bar in Chicago,” Old Town Ale House is a great spot for a chill night out with the guys. This cash-only watering hole is known for its jukebox and old-school vibes, plus was also dubbed a favorite of Anthony Bourdain. For a quirkier scene, The Rec Room is a basement bar made to feel like a house party. Take advantage of the disco ball, dance floor, and a fridge stocked with can beers, fried chicken, pizza, and more.
Where to Stay
Situated in the River North neighborhood, Hotel Felix is all about eco-friendly accommodations and a sleek, modern atmosphere. You’ll also find a restaurant, bar, sushi eatery, and coffee shop on-site for the ultimate convenience.
Once an exclusive sportsmen’s club, the Chicago Athletic Association is now a premier hotel located just steps away from Millennium Park. This spot is practically made for a Chicago bachelor party with an upscale game room (think bocce bay, billiard, and shuffleboard tables), historic speakeasy, rooftop bar, and even a Shake Shack location all within the property.