Name: Vespertine Takes Over The Hole
Start: 2026-05-25T13:00:00-05:00
Location: Jackhammer

Chicago's LGBTQ+ community is this incredible mix of genuine people from all walks of life who've built something really special here—it's the kind of place where you can be yourself without any of the pretense you might find elsewhere. The city has this deep history of queer culture and activism that you can feel in the neighborhoods, and there's a real sense that everyone's welcome to bring their whole authentic self to the table.

The scene here is beautifully diverse, with everything from laid-back neighborhood bars like The SoFo Tap and Roscoe's Tavern where you'll run into regulars who actually know your name, to spots like The Rabbit Hole and Replay Lakeview that have their own unique vibe and energy. What really makes Chicago's LGBTQ+ spaces special is that they feel like genuine community gathering spots rather than just places to go out—you'll find people actually connecting, dancing, laughing, and building real friendships night after night.

Chicago

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Queen for the Night: Patron Turnabout Show

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Draglicious Drag Revue

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Sunday Funday Show Tunes

Tighty Whities Sunday Bunday!

Poker in the Bottom

Bearaoke

Sunday After Dark

Chicago House TransSafe Drop In

Make Mondays Suck Less

Floq Adult Support Group

Queer Movie Monday: Stud Life

Musical Monday: Show Tunes

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Serve! Vocal Edition Karaoke

Golden Diners Hot Meals

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Dragonflies Support Group

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Jeopardy! Bar League Trivia

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Queer Book Club: "Fruit Fly" by Josh Silver

Trivia Tuesday: Pokémon Edition

Young Adult Drop-In

Youth Support Group (Grades )

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Broadway Boulevard

Lip Service Karaoke

House of Couture Thursdays

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Saturday Night Dance

Mrs. & Mrs. Claus Debut at Dorothy!

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Latin Night: All Latin All Night with Jenny Fox

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Debuts ft. Folie & DJ Ariam Perez Hilton

Sleigh Belles Bottomless Drag Brunch

Memorial Day afternoon takeover of Jackhammer's legendary subterranean space by Vespertine Chicago, a queer women's, trans, and non-binary community focused on education and exploration in fetish and BDSM. Interactive hands-on learning, safe scene play, and a strict fetish dress code (leather, PVC, uniforms, goth, rope, neoprene — no latex). Toy bags welcome, complimentary bag check available. 21+ with valid ID required. $30 advance tickets only.

Vespertine Takes Over The Hole

Chosen Family

Leather & Kink Culture

On Monday, May 25th at 1:00 PM, Memorial Day afternoon takeover of Jackhammer's legendary subterranean space by Vespertine Chicago, a queer women's,

Memorial Day afternoon takeover of Jackhammer's legendary subterranean space by Vespertine Chicago, a queer women's, trans, and non-binary community

Vespertine Takes Over The Hole at Jackhammer

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Memorial Day afternoon takeover of Jackhammer's legendary subterranean space by Vespertine Chicago, a queer women's, trans, and non-binary community focused on ...

Vespertine Takes Over The at Jackhammer, Chicago – May 25

21 Plus

Community Focused

fetish

Interactive

kink

Leather Bar

Jackhammer has been a cornerstone of Chicago's leather and alternative scene for over 20 years — a no-judgment space where self-expression isn't just tolerated, it's celebrated. The vibe is unpretentious and genuinely welcoming across the board: pool, darts, a solid dance floor, daily drink specials, and an outdoor patio that fills up year-round. This is the kind of neighborhood bar that knows exactly what it is and does it well.

Vespertine Takes Over The Hole

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