Part of the Gay Chicago Guide — bars, events & things to do.
Saturday, June 27, 2026
Northalsted's Business Alliance throws its annual Pride bar crawl, and it's the most fun way to take in the neighborhood at full Pride-weekend tilt. The afternoon kicks off at 1pm at Sidetrack, then winds through the strip's most iconic stops — Progress, Hydrate, North End, Splash, Replay, Lucky Horseshoe, Cell Block, Kit Kat and more — with a commemorative collectible waiting at each one. Grab your crew, pull on your brightest rainbow, and tour the rainbow through Chicago's proudest neighborhood.
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Tue, Jun 16
8 PM - 10 PM
Sidetrack, Chicago
Test your Pokémon knowledge at Sidetrack's weekly trivia night. No cover, frozen cocktails, and friendly competition every Tuesday on Halsted.
Wed, Jun 17
6 PM - 9 PM
Sidetrack, Chicago
Monthly wrestling happy hour at Sidetrack. Wrestling gear encouraged, clothes check available. Meet wrestlers, kinksters, and enthusiasts.
Wed, Jun 17
9 PM - 2 AM
Sidetrack, Chicago
Monthly Lady Gaga dance party at Sidetrack Chicago. Drag performances, videos, and dance-offs every Wednesday. LGBTQ+ nightlife.
MonthlyThu, Jun 18
5:30 PM - 7:30 PM
Sidetrack, Chicago
Network with LGBTQ+ professionals at Sidetrack Chicago. $20 entry includes two drinks and a raffle ticket. Proceeds benefit Alma Chicago.
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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.
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