← Part of International Mr. Leather
Part of the Gay Chicago Guide — bars, events & things to do.
Saturday, May 23, 2026
Get ready for a leather-fueled celebration with an IML-inspired DILF party for men over 35 and the men who love them. Expect a high-energy late-night scene with DJ beats and dancing that'll keep you moving until the early morning hours. Whether you're a seasoned leather enthusiast or just curious about the daddy scene, this fun and inclusive event welcomes all to strut their stuff and connect with the community. Grab your best leather look, hit the dance floor, and experience the perfect blend of grit, glamour, and good vibes. This event was imported by Out x Out. Please visit the venue link to verify details.
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Mon, Sep 21
10:30 PM - 12:30 AM
Hydrate Nightclub, Chicago
Hydrate's weekly Monday drag show in Chicago, hosted by Ms. Ruff N Stuff with beats by Martin — doors at 8pm, show starts at 10:30pm.
Weekly
Tue, Sep 22
6:30 PM - 9 PM
Cell Block, Chicago
Every Tuesday at Cell Block, Chicago's leather bar — doors close at 7:30pm for an evening of uninhibited fun at the city's most unapologetic leather space.
Monthly
Wed, Sep 23
7 PM - 10 PM
Whiskey Girl Tavern, Chicago
Weekly queer country line-dancing night at Whiskey Girl Tavern, Edgewater, Chicago. Free, Wednesdays.
Wed, Sep 23
9 PM - 2 AM
Sidetrack, Chicago
All Things Britney & Rihanna hits Sidetrack Sep 23 — a pop-princess double-feature video dance party from 9pm-2am on Halsted.
Thu, Sep 24
6 PM - 10 PM
Rockwell on the River, Chicago
Gerber/Hart Library & Archives marks 45 years with an anniversary gala at Rockwell on the River, Chicago, Sept 24.
Thu, Sep 24
6 PM - 10 PM
Jackhammer, Chicago
Bear Happy Hour at Jackhammer, Chicago
MonthlyLet people know you're going, see who else is attending, and share the event with friends.
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