New York's First Japanese Speakeasy Restaurant is a Hidden Gem
Home of the Saturday Drag Matinee
Berlin opened up in the ‘80s as a refuge for artsy or alternative types, and you’ll still find plenty of those folks on the floor today in this dark, underground-esque space. It’s one of the most welcoming LGBTQ clubs you’ll find, with plenty of room for members of the community and their allies. If you’re going for the first time, make sure it’s on a Saturday night for its Drag Matinee, featuring queens from around the world (and right here in Chicago) followed by a DJ set into the wee hours.
For super-fun takeover nights
Every Sunday, Scarlet is the place to be, all day long. Start the week off right with their Liquid Brunch (doors open at 2pm), featuring $10 bottles of Champagne and other crazy-good drink specials. Later on, dance the night away with the bar’s famous takeovers, including such favorites as Selena, Beyonce, Rihanna, and more. This is one of the smaller must-see spaces in Boystown, meaning the more you go, the more you’ll start running into the same people and feeling like a part of a real community.
Chicago's original gay bar is still great
Little Jim’s opened in Boystown in 1975 as Chicago’s first gay bar, and it’s still in business today. It’s a dive where you’ll likely find a more mature crowd than at a spot like Scarlet. The recently opened Big Jim’s is attached and serves pretty good, reasonably priced bar food, making it easy to fuel up on your next date or night out with friends.
The quintessential club experience
When you walk into Progress, you’re greeted by a sleek bar, a gigantic, funky (but in a very clean and modern sense of the word) chandelier and a ton of space to dance. This is one of the classier clubs on Halsted, but don’t worry, the dance floor is still wild. On weekends, it’s rare not to see a line out the door, but it always moves quickly and is well worth the wait if your goal is to move to some of the best music in Boystown.
A recently renovated Boystown staple
Roscoe’s has been a Boystown staple for three decades, and it’s easy to see why. It offers the best of all worlds: a small bar for the lovers of dives and a dance room for those looking for more of a club atmosphere. Plus, there’s great outdoor space for patio fanatics. It recently underwent renovations that brought the bar up to date and enhanced its sound system for maximum musical impact.
The city’s largest "black LGBT club"
This is another South Shore gem, a place where you can get down on the dance floor to house DJs, hip-hop, old-school hits, and more on a killer sound system (and a new video system added just a few months ago). Their dance floor currently isn’t super huge, but soon an all-new dance hall will open up next door, taking your nights at this club to a whole new level.
Your friendly neighborhood spot
Are you tired of hearing about Boystown yet? While the Lakeview sub-neighborhood is the go-to spot for late-night LGBTQ-friendly clubbing and LGBTQ-owned businesses, Big Chicks in Uptown is one of the city’s gems when it comes to laid-back, friendly neighborhood bars that happen to offer a little something extra for the LGBTQ community. Come here for delicious burgers and drinks, Drag Race viewing parties, and just general no-frill friendliness. This spot has been around for 30 years for a reason.
The must-go spot in Chicago’s "other" LGBTQ neighborhood
Boystown is loud about its LGBTQ roots (rainbows everywhere!), but Andersonville has a quieter pride in being a particularly LGBTQ-friendly neighborhood, and Hamburger Mary’s represents that attitude perfectly. It’s a good old-fashioned neighborhood burger joint, but it also features weekend drag shows, Bingo, cabaret theater, trivia, and more, all in three spaces that offer a little something for everyone: a classy dining room with an outdoor patio, an upstairs cabaret lounge and a sports bar and brewpub. Check out the whole space for a laid-back, authentic Chicago experience.
Chicago’s only black-owned gay bar
Contrary to what many North Siders might try to tell you, you don’t have to be on the North Side to hang out in super cool LGBTQ bars. The Jeffery Pub on South Shore is the only black-owned gay bar in Chicago, and it typically plays hip-hop, house, R&B music, and live entertainment -- and puts on some of the most fun drag shows you’ll ever witness.
A huge, multi-room must-see
Sidetrack opened to humble beginnings in 1982 at about the size of a one-bedroom apartment. Since then, it has added a rooftop bar, deck, lounge, and more -- taking over eight storefronts and multiple levels and boasting the ability to host about 1,000 people at once. The bar throws viewing parties for shows like RuPaul’s Drag Race and Will & Grace, as well as takeover nights featuring artists like Lady Gaga and Beyonce.
An LGBTQ headquarters way up north
If you’re trying to go out way up north in Chicago, the Jackhammer Complex is the place to be. It features three bar spaces ("Dance," "Sports," and "Fetish") and a patio, as well as an attached adult shop called Leather 6410. Swing by for drag shows, karaoke, live music, dancers, fetish events, and DJs. But you definitely don’t want to miss this spot’s monthly underwear party and contest, so be sure to check the calendar before you plan your visit here.
A night club with a taste for great DJs
Hydrate has been open for 15 years now, and in that time it has built a reputation for itself as the go-to place for lovers of great dance music. Hit it up on the weekends to experience that side of things, or go on a Wednesday night for its Honeys on Halsted drag show. No matter when you go, you’re in for a great, late night.