Part of the Gay Chicago Guide — bars, events & things to do.
Friday, August 14, 2026
Kick off your Friday with an all-night celebration of show tunes, drag, and dance at Sidetrack! Start with three hours of your favorite musical theater hits, then catch RuPaul's Drag Race All Stars before the dance floor takes over for the Friday Night Dance Party. With no cover charge and the rooftop opening early evening, it's the perfect way to transition from happy hour into a night of pure LGBTQ+ celebration and community vibes. This event was imported by Out x Out. Please visit the venue link to verify details.
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Sat, Aug 8
2 PM - 4 PM
Sidetrack, Chicago
Dorinda Medley of RHONY meets fans 2-4pm in Sidetrack's Side Bar during Market Days Saturday, then joins Boy J and Veronica Pop on stage.
Sat, Aug 8
3 PM - 6 PM
Sidetrack, Chicago
SaturGay Drag & Games takes over Sidetrack 3-6pm on Market Days Saturday — drag, games, and festival-weekend energy on Halsted.
Sat, Aug 8
8 PM - 3 AM
Sidetrack, Chicago
Sidetrack's Saturday Night Dance Party goes 8pm-3am on Market Days Saturday — dance floors and video bars in the heart of the festival.
Sun, Aug 9
1 PM - 7 PM
Sidetrack, Chicago
Weekly Broadway sing-along at Sidetrack's Main, Cherry & North Bars. Theater lovers and LGBTQ+ community celebrate Show Tunes Sundays with dancing and good vibes.
WeeklySun, Aug 9
2 PM - 4 PM
Sidetrack, Chicago
Drag Race star Plane Jane meets fans 2-4pm in Sidetrack's Side Bar on Market Days Sunday, then performs with Sasha Love and Amber Valentine Marks.
Sun, Aug 9
7 PM - 2 AM
Sidetrack, Chicago
Weekly gay dance party at Sidetrack in Chicago's Northalsted. High-energy beats, music videos, and frozen cocktails every Sunday night.
WeeklyLet people know you're going, see who else is attending, and share the event with friends.
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