Best gay bars in Chicago

Boystown is the historical center of Chicago’s gay scene, but great gay bars can be found from downtown to Uptown
Photograph: Christopher Kitahara
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Chicago has a vibrant gay bar scene, and has for decades. Much of it is clustered around a half-mile stretch of North Halsted Street and Broadway in East Lakeview, long known as Boystown. The gay bar culture started there with Little Jim’s in 1975, and followed over the next decade by many bars now long since gone and others, like Sidetrack and the North End, that have survived for decades. These days, Boystown is still a prominent gay playground, but queer-courting bars have spread into many other neighborhoods—and the definition of “gay bar” has greatly expanded, too. From dance clubs to dive bars to sports bars, there’s an LGBTQ-oriented watering hole in Chicago to fit every interest. These are some of our favorites.

RECOMMENDED: Drink at the best bars in Chicago

Best gay bars in Chicago

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0513.chi.rb.at.Sidetrack.jpg
Bars, Cocktail bars

Sidetrack

icon-location-pin Boystown

If size matters, there’s no better bar in Boystown than this hot spot. Six big rooms and a gorgeous rooftop deck are all packed with cute, frisky boys distracting themselves with the same three things: the videos on the wall, the drink in their hand and the ass in your jeans. Enjoy the signature slushie drinks carefully—you don't want brain freeze to impair your flirting.

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Bars, Dive bars

Big Chicks

icon-location-pin Uptown

Not a Boystown fan? Skip the stand-and-model parade and head to this laid-back Uptown saloon, where community matriarch Michelle Fire serves tasty victuals to sunburned boys and girls at her famous Sunday buffets and keeps the rest of the week happening with tons of food and drink specials (like buck burgers on Mondays) and all-out dance parties on weekends.

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Clubs

Berlin

icon-location-pin Lake View

This freak-friendly dance destination in Lakeview built its reputation back in the mid-’80s with a mix of German new-wave music, art installations and even transvestite shows. These days, it’s still quirky but more retro, with diva-tribute, disco and ’80s nostalgia nights. Goths and gays are extra welcome, but the scene here is made up of almost everyone. Thursday night’s Stardust is a major locus of nightlife creativity.

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Bars, Dive bars

The Closet

icon-location-pin Lake View

This teeny taproom is a good stone’s throw from the hustle and muscle of Halsted Street’s rowdy boy bars, and that’s just the way this clientele likes it. Plenty of ladies hang here until the midnight hour, but the boys crash the party shortly thereafter, creating one of the few truly mixed queer scenes in the city.

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Bars, Cocktail bars

Roscoe’s Tavern

icon-location-pin Lake View

This longstanding landmark has multiple bars, a dance floor, an outdoor patio and all the Lady Gaga you desire, so the Boystown gay bar brings a lot to the table. The drink specials are the best in the neighborhood, with $15–$17 cocktail pitchers, $5 shots and bombs each day and $1 Miller Lites on Sundays. Roscoe’s is also a favored venue for visits by current and past RuPaul’s Drag Race personalities.

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Bars, Cocktail bars

Wang’s

icon-location-pin Lake View

After Henry Chang got a liquor license for his formerly BYOB eatery Wakamono, he promptly built one of Boystown’s best bars. The intimate space is, like all of Chang’s projects, highly stylized, employing lush, floral wallpaper and woodwork the likes of which you’ve seen only in an opium den. It might be a restaurant bar, but it has a style, vibe and—thanks to refreshing pear martinis—a taste all its own.

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Replay in Andersonville
Bars, Lounges

Replay Andersonville

icon-location-pin Andersonville

The Andersonville outpost of the Boystown beer-and-bourbon arcade bar adds food to the mix, with burgers, brunch and more to fuel your retro gaming. The bar runs down the center of the space, though it's just one-sided—the other side of its rear wall is lined with video game consoles. The extensive beer list (26 rotating drafts listed on a giant chalkboards over the bar) and even bigger collection of bourbons are the reasons to visit, other than getting it on like Donkey Kong, of course.

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Photograph: Evan Jenkins
Bars, Pubs

D.S. Tequila Company

icon-location-pin Lake View

If you frequented the now-departed “luxe lounge” known as minibar, you know that its former owners Stu Zirin and John Dalton are no masters of subtlety. Witness, as further evidence, their more recent venture, D.S. Tequila, whose name (we’re pretty sure) refers to the sex act the Dirty Sanchez. The interior boasts a menu of boozy frozen margaritas and decent tacos and burgers. The only thing understated about the place is the outdoor patio, where twinkling colored lights give off a serene urban vibe.

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Bars, Cocktail bars

Progress Bar

icon-location-pin Boystown

Progress, in the former Cocktail space, boasts a cloud-like overhead sculpture installation made up of 19,000 twinkling light bulbs. It also boasts a better selection of craft beers on tap than most bars on the Halsted strip, pouring elixirs like Magic Hat #9 and local brew Half Acre Daisy Cutter.

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Bars, Lounges

Elixir

icon-location-pin Lake View

At this shoebox of a cocktail bar, the drinks are skillfully prepared, the crowd is kept to a minimum by the doorman, and the music never gets so loud that it drowns out your insights on Jean Genet. The clientele is mixed in age but not in gender, and everyone is on their best behavior, which makes it an altogether more sophisticated and adult experience than Elixir’s next-door sister, Hydrate.

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Photograph: Max Herman
Bars, Dive bars

Second Story Bar

icon-location-pin Streeterville

You wouldn’t believe the brand of tie-loosened debauchery that happens at this fantastic dive on a nightly basis. Unless, of course, you climb the carpeted stairway—following the thumping bass and uninhibited laughter coming from behind the heavy, unmarked door—and step inside. Once you see this place, you’ll believe anything.

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Photograph: Marina Makropoulos
Bars, Lounges

Marty’s Martini Bar

icon-location-pin Andersonville

This upscale Andersonville martini lounge burns through olives and vermouth faster than a steakhouse does. These Don Drapers come in all types, but it seems the straight folk tend to show up first for a predinner cocktail and the gay crowd comes later. Like gentrification, but in reverse.

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Camera
Bars, Sports Bars

The North End

icon-location-pin Boystown

Chicago gays pay just as much attention to sports as their hetero counterparts, and at this Boystown bar you can not only cheer on the Bears, the Cubbies and other local faves, but also partake in pool and dart tournaments. Did we mention this place is practically attitude-free? That’s an added bonus in our books.

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Club Escape
Photograph: Michael Jarecki
LGBT

Club Escape

icon-location-pin South Shore

Thanks in part to an ebullient drag show hosted every Tuesday, Wednesday and Saturday by the legendary Mz. Ruff ’n’ Stuff, this club wins the blue ribbon among South Side queer bars. The drinks are cheap and stiff, the genders are evenly mixed, and the live acts are off the charts. One devotee informed us the club is popular with the south suburban crowd, has a core following of white dudes, and is especially popular on Friday and Sunday nights.

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Photograph: Jaclyn Elizabeth Rivas
Bars, Lounges

Jackhammer

icon-location-pin Rogers Park

A construction theme dominates this Rogers Park gay bar, where a grab bag of dudes cram the dance floor on weekend nights. If you can lure yourself away from the constant porn, a beautiful outdoor patio beckons with a psychic on hand to predict that the guy you’re about to take home is probably not the same one you’ll be introducing to your parents one day.

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Hydrate
Bars, Lounges

Hydrate

icon-location-pin Lake View

Hot and sweaty boys pack themselves in like gay sardines for all-night dancing at this thumpin’ after-hours club. A rotating menu of shenagigans includes the Honeys on Halsted Drag Show, RuPaul’s Drag Race viewing parties and more. Recent renovations have carved out a space for live theater.

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Jeffery Pub
Photograph: Michael Jarecki
Bars, Pubs

Jeffery Pub

icon-location-pin South Shore

The entry process is rather rigorous (we had to be buzzed in and then patted down), but it’s worth it for strong drinks and a friendly LGBTQ vibe. On a recent visit we watched the crowd groove to hip-hop and house while also chatting and canoodling on the sidelines.

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Bars, Beer bars

SoFo Tap

icon-location-pin Uptown

What’s not to like about this cozy corner tavern? The enclosed beer garden is adorable, pooches are welcome and there are regular entertainments, like game show nights and pub quizzes. As for the clientele, it’s mostly thirty- and fortysomething gay dudes. But at SoFo, everyone is welcome.

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KitKat
Restaurants, American

Kit Kat Lounge

icon-location-pin Lake View

If you don’t know who Marilyn and Joan are, don’t bother. This slick nightspot only gets campier with age, so prepare to be entertained by black-and-white Hollywood glamour movies and performances by female impersonators of Hollywood icons. The 100-martini-strong drink list is a draw, and chef Joann Witherell puts the focus on dishes like bacon-truffle mac and cheese and Southern fried chicken with cayenne maple waffles. But you didn’t actually come here for the food, did you?

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LGBT

@mosphere

icon-location-pin Andersonville

Boy bar @tmosphere put Andersonville on the gay male map when it opened its door in 2002. These days, it’s mostly a low-key place to have a beer with one of your mates, although on weekends the thump-thump of the DJ keeps the go-go boys shakin’ and the crowds stirring.

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Dawn Anthony at Scot's
Bars, Pubs

Scot’s

icon-location-pin North Center

Ties may be loosened and the blazers may come off, but it’s still pretty much business class during the week at this casual corner hang in Ravenswood. Indoor plants and holiday-themed decorations add to the office-party vibe, but make no mistake: These guys are champion softball players, so they know how to play the game.

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Bars, Pubs

The Glenwood

icon-location-pin Rogers Park

At first glance, this place looks like your typical yuppie sports bar, but the vastly male clientele, plum and ochre walls adorned with abstract art, and Kylie Minogue soundtrack reveal it to be Rogers Park’s straightest-acting gay bar. It’s also dog-friendly and offers a nice selection of retro cocktails like sidecars and lime rickeys.

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