Part of the Gay Chicago Guide — bars, events & things to do.
Saturday, June 20, 2026
Join Sidetrack's Pride Fest celebration featuring a free meet and greet with Real Housewives and Traitors star Candiace Dillard Bassett, plus drag performances from Boy J and Veronica Pop across the afternoon and evening. No cover charge to get in—grab one of those legendary frozen cocktails and soak up the high-energy celebration across Sidetrack's seven connected rooms and bars. Whether you're here for the celebrity moment, the drag performances, or just to be part of Chicago's queer community gathering at an iconic venue, this is Pride done right on Northalsted. This event was imported by Out x Out. Please visit the venue link to verify details.
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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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