Part of the Gay Chicago Guide — bars, events & things to do.
Tuesday, August 18, 2026
Put your trivia skills to the test at this weekly brain-battle hosted by Stew, where you'll compete alongside the Sidetrack crowd for bragging rights and glory. After trivia wraps, stick around as the venue shifts into high gear with Pop Favorite Videos lighting up the big screens—the perfect soundtrack to keep the energy flowing all night. Whether you're a trivia champion or just here for the music and the vibe, it's the ideal midweek escape to celebrate with Chicago's vibrant LGBTQIA+ community. This event was imported by Out x Out. Please visit the venue link to verify details.
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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.
Wed, Oct 21
6 PM - 9 PM
Sidetrack, Chicago
Undercover Wrestler meets at Sidetrack every third Wednesday 6-9pm — a free social for wrestlers and fans with gear encouraged and clothes check.
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