Part of the Gay Chicago Guide — bars, events & things to do.
Monday, August 24, 2026
Kick off your week with your favorite show tunes at Sidetrack's legendary Musical Monday, where classic theater hits light up the big screens in all their glory. Whether you're belting along to Broadway classics or discovering new favorites, this high-energy celebration brings together Chicago's LGBTQIA+ community for a night of song, dance, and pure theatrical joy. Grab a frozen cocktail, settle into the energetic vibe, and let the music carry you through the night. This event was imported by Out x Out. Please visit the venue link to verify details.
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Tue, Aug 18
8 PM - 10 PM
Sidetrack, Chicago
Weekly trivia night hosted by Stew at Sidetrack, followed by Pop Favorite Videos. Compete for bragging rights with Chicago's LGBTQ+ community every Tuesday.
Wed, Aug 19
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.
Monthly
Wed, Aug 19
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, Aug 20
9 PM - 2 AM
Sidetrack, Chicago
Let's Go! Latin returns to Sidetrack Aug 20 — Latin pop and dance videos 9pm-2am across the Main, Cherry, and North Bars.
Fri, Aug 21
4 PM - 9 PM
Sidetrack, Chicago
Weekly Friday show tunes party at Sidetrack Chicago. Video dance party, frozen cocktails, drag race viewing, and dancing. Start your weekend with the gay community.
WeeklyFri, Aug 21
9 PM - 2 AM
Sidetrack, Chicago
Weekly gay dance party at Sidetrack in Chicago's Northalsted, running 9pm to 2am every Friday after the afternoon Show Tunes set.
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