Part of the Gay Chicago Guide — bars, events & things to do.

Thursday, May 21, 2026
Join the community for Dad's Den: Cigar Social, a laid-back gathering during IML Weekend brought to you by the IML Weekend Cigar Society and the Leather Archives & Museum. This is your chance to connect with fellow leather and fetish enthusiasts in a welcoming space that celebrates and explores queer culture. Light up, kick back, and embrace the camaraderie that makes Chicago's leather community so special. This event was imported by Out x Out. Please visit the venue link to verify details.
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Wed, Jun 24
9 PM - 1 AM
Jackhammer, Chicago
Weekly Wednesday karaoke at Jackhammer in Rogers Park. High-energy performances, $4 well drinks, and a bold queer community. Hosted by Tim Bell.
Weekly
Thu, Jun 25
6 PM - 10 PM
Jackhammer, Chicago
Weekly bear happy hour at Jackhammer during International Mr. Leather weekend. Connect with the bear community in one of Chicago's gay spaces.
Monthly
Fri, Jun 26
9 PM - 4 AM
Jackhammer, Chicago
Leather and gear dance party at Jackhammer. High-energy queer nightlife celebrating fetish, kink, and bold self-expression every Friday.
Monthly
Sat, Jun 27
1 PM - 5 PM
Jackhammer, Chicago
Queer women, trans, and non-binary play party in Jackhammer's basement. Sex-positive, inclusive space for Chicago's LGBTQ+ community to connect and express.
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Your complete guide to LGBTQ+ Chicago — the best gay bars, annual events, neighborhoods, hotels, and things to do in the Windy City.

It's Chicago Pride weekend. The 55th Pride Parade rolls down Halsted on Sunday under the “Free to Be Proud” banner, and we mapped 78 events to get you there — Pride power hours at Scarlet, a Men's Room glow party at Sidetrack, drag brunches at Roscoe's and Kit Kat, and parade-day parties up and down Boystown.

A neighborhood-by-neighborhood map of gay and gay-friendly Chicago — the vibe, the bars, and what it's actually like to live in each, from Boystown to the South Side.
