Brunch … but manly
Chicago has plenty of brunch spots, many of which offer bottomless drink options or specials to get the party started. Check out Bub City for heavier fare and a create-your-own Bloody Mary bar. Also check out The Biscuit Man in Lakeview. Set inside The Long Room, The Biscuit Man serves hearty bowls and customizable sandwiches that will have you well prepared for a day of alcohol-accompanied activities.
Where to stay
Most every Chicago neighborhood has outstanding restaurants, bars, and activities to offer. When figuring out where to stay, it might be best to choose your activities first and then consider what you want to have within walking distance. However, if the lodging of choice is a bit out of the way, it’s no problem; in the city, chances are there’s a nearby “L” or bus stop, or you can always Uber or Lyft.
On a budget
Hotel rooms in Chicago don’t generally come cheap. If you’re working within a budget, Airbnb might be a good alternative, especially if everyone wants to stay together. There are many places available across the city.
A typical Chicago hotel room will probably run between $200 and $400 per night. Consider ACME Hotel in River North for a hipster vibe with all the gadgetry you could possibly require, complete with an Amazon Echo. ACME also offers the Hair of the Dog and the Guys Getaway packages, which seem tailor-made for bachelor parties.
For truly luxe lodging try the Waldorf Astoria in Gold Coast (and you can counteract the luxury with the close proximity to the late-night dive bars). The hotel offers one- and two-bedroom suites, so depending on how many people there are, the party might be able to share the space – and the expense. Waking up in 400-thread-count sheets is sure to dull the ache of the inevitable hangover.
From the many festivals to the music venues, and more, Chicago is filled with events in the summer. Be sure to check out one-time and annual events that might occur while you’re in town. Here are a few classics that are always a good time.
Rent a boat on Lake Michigan
Lake Michigan offers a lot in terms of activities, and the Midwest beaches get the job done surprisingly well. For a day on the water, check out Boatsetter. Described as an Airbnb for boats, owners will rent out their boats when they’re not using them, and some will even captain them for you. Whether fishing, cruising, or drinking is your goal, there’s a boat for you.
There’s a reason the Daily Herald nominated Arlington Park as a 2018 Readers’ Choice Best Bachelor/Bachelorette Party Venue. Take the Metra rail or grab a cab and head to nearby Arlington Heights to place bets on the horse races or to simply take in the sights with a drink in hand. The park offers food and drink packages for large groups and special events, so be sure to inquire.
Take in a baseball game
Chicago has some die-hard baseball fans, as was evidenced when the city dyed the Chicago River blue when the Cubs won the world series in 2016 after more than a century without a pennant. Whether rooting for the Cubs or the White Sox, a baseball game in Chicago is always a fun experience with the boys.
With wood-paneled interiors, a meat-centric menu, and an extensive drink list inclusive of beer, wine, cocktails, and spirits, upscale gentlemen are sure to enjoy GT Prime. For a casual night of pizza and beer on the perfect patio, head to Parlor Pizza Bar in West Loop or Wicker Park. To refuel with tacos and margaritas on your way to the next bar, try Wicker Park’s Big Star. You might have to wait for a table, but this Chicago classic is well worth it. For dinner, or for a pick-me-up later on, head to award-winning Au Cheval in West Loop for fare that redefines diner food.
Where to drink
Now the real party begins! Chicago has a long list of bars and clubs that offer something for everyone, including a few that have activities other than drinking, just in case some of the boys need a breather. For arcade games with a full bar, try Headquarters Beercade in River North, or start a ping-pong tournament at AceBounce or SPiN. Stop by Kingston Mines blues club in Lincoln Park for live music with extensive beer and cocktail lists. For more of a club atmosphere, try Joy District, which is known for its outstanding rooftop, or head to nearby Studio Paris Nightclub. For a late-night ’90s dance party, Innjoy in Wicker Park or Logan Square is the place.