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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Sun, Sep 13
9 PM - 2 AM
Sidetrack, Chicago
Weekly late-night dance party across Sidetrack's four bars. No cover, multiple dance floors, party music until early morning. Every Sunday.
Weekly
Mon, Sep 14
8 PM - 2 AM
Sidetrack, Chicago
Weekly Broadway singalong at Sidetrack Chicago. No cover, high-energy show tunes night where the whole gay bar sings together. Every Monday.
WeeklyTue, Sep 15
8 PM - 10 PM
Sidetrack, Chicago
Weekly trivia hosted by Stew at Sidetrack gay bar. No cover, pop videos until 2am, seven connected rooms. Laid-back weeknight vibe.
Weekly
Wed, Sep 16
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.
MonthlyWed, Sep 16
7 PM - 9 PM
Sidetrack, Chicago
Monthly
Wed, Sep 16
9 PM - 2 AM
Sidetrack, Chicago
Monthly Lady Gaga dance party every Wednesday at Sidetrack gay bar in Chicago. Dance floors, live energy, and a community of Gaga fans celebrating together.
MonthlyLet people know you're going, see who else is attending, and share the event with friends.
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