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Photograph: Leon Andrew HensleyCandy Shop at Evil Olive

After-hours gay Chicago

Seven nights on the town reveal a wilder side to queer nightlife.


In line for a drink at Circuit Nightclub (3641 N Halsted St), a woman with slicked-back hair slowly dry humps her girlfriend from behind while blowing fat, pink bubbles with her gum. It’s after 2am at the Black Bra Party and the first of seven back-to-back late nights I’m spending on the town. Although Chicago’s lady scene is small, it’s also diverse, and the dance floor is crowded with shirtless women of various ages and ethnicities undulating to “Teach Me How to Dougie” by Cali Swag District. I run into an acquaintance who tells me the party is a bust and that everyone is complaining (although the swelled masses indicate otherwise). At sibling bar Rehab, a lady nods off next to me. I feel her pain.

A tall and glittery Cyon Flare looms large over the crowd at Hydrate (3458 N Halsted St), where the lights are dimmed for its monthly Blackout party. Glowsticks, those ancient relics from the ’90s, abound, and the place is packed with smooth shirtless dudes (chest hair is apparently an endangered species in Boystown). By 3am the crowd has shifted into pushing and shoving mode, so I hit Diva Thai and Sushi Bar (3542 N Halsted St) for witching hour dragon rolls. The food is good and only the circles under my server’s eyes dim this cheery place. By 4:30am, I’m being hit on relentlessly by a cute black guy at Little Jim’s (3501 N Halsted St) who promises me he’s “super attractive and easy.” The joint is rocking, but last call is at hand.

The crowd is thin at Candy Shop, a weekly queer party at Evil Olive (1551 W Division Ave) where club kid JoJo Baby is dressed like a dog and grooving to retro jams like “Electric Avenue” and “Private Eyes” while the bar staff from Scarlet cavorts at a table nearby. It would be nice to see this newbie night take off, but since it hasn’t by well after 2am, I head to the Closet (3325 N Broadway), where someone has just dropped a glass—proof that we’ve entered the shit-show hour. A perfect 25 to 30 people are imbibing and chatting, and I decide this is my new favorite Closet night.

“I’m pretty sure I paddle like a girl,” a handsome, young white guy whispers in my ear at Berlin (954 W Belmont Ave). He and some Asian stud have been taking turns spanking a grinning lad who is bent over one of the stages with his pants down. Meanwhile a straight girl, high on booze and cocaine, is biting me hard on the neck. It’s chill at Perv, a themed night of fetish (Berlin has since closed Mondays). By 3:55am, the biter has taken her pants down and is helping herself to a few floggings. I exit for taqueria Tradicion (958 W Belmont Ave) then head home to apply a bandage to my neck wound.

At late-night fixture Jackhammer (6406 N Clark St), the sound of karaoke crooners in the front room catapults me instead to next-door neighbor Touché (6412 N Clark St). Aside from a few black dudes in back, I’m the lone patron hunkered over the bar at 2:30am. The blasting of “Too Much Time on My Hands” by Styx over the loudspeakers offers an appropriate soundtrack for the night, and I accept a shot from the bartender but decline his invitation to get naked. I call it an “early” night.

Just like at a Vegas casino, time evaporates at Steamworks (3246 N Halsted St). Wandering its labyrinthine hallways clad only in a white towel, I realize it could be 3, 4 or 5am; I really have no idea. A soak in the bubbly first-floor jacuzzi feels great although the action is clearly on the second floor, where about two dozen men are on the make. A white, mustached hipster strikes up a conversation with me and politely asks if he can touch my cock. It’s nice to be wanted, even at dawn.

It’s 2:01am and my face is pressed against the front door at a nearly empty Charlie’s (3727 N Broadway). I’ve just come from Avondale’s Late Bar (3534 W Belmont Ave), which hosted its second monthly LGBT dance party; there weren’t enough queer people there to justify sticking around. I hit the new Pie Hole (3477 N Broadway) for some late-night nosh, but it’s already closed. Tonight’s a bust, although after this tiring week there’s still one place left I’m dying to go, and that’s home.

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