Part of the Gay Chicago Guide — bars, events & things to do.

Tuesday, June 30, 2026
A special Madonna-themed edition of Trivia Tuesday celebrating release week for her new album CONFESSIONS II.
Have feedback on this description? Let us knowLet people know you're going, see who else is attending, and share the event with friends.

Tue, Jun 30
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.
Weekly
Wed, Jul 1
9 PM - 2 AM
Sidetrack, Chicago
Monthly Taylor Swift night at Sidetrack Chicago. Five hours of music videos, drag performances, and dance-offs with the LGBTQ+ community. Every Wednesday.
Monthly
Thu, Jul 2
9 PM - 2 AM
Sidetrack, Chicago
Monthly Thursday pop dance party at Sidetrack Chicago. Drag performances, pop hits from Chappell Roan, Charli XCX, and more across three bars.
Monthly
Fri, Jul 3
3 PM - 2 AM
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.
WeeklyCatch your city's vibe or the global LGBTQ+ scene.
No spam, unsubscribe anytime.

Your complete guide to LGBTQ+ Chicago — the best gay bars, annual events, neighborhoods, hotels, and things to do in the Windy City.

Pride South Side, holiday-weekend parties, and the Black & Brown LGBTQ+ bars that carry the scene year-round — your Chicago Black Pride 2026 guide.

Andersonville is Chicago's brunch-and-boutiques gayborhood — residential, queer-women-friendly, and built around independent shops, not bottle service. Here's the local's guide.

From the 1924 Society for Human Rights to the Legacy Walk's rainbow pylons, here's Chicago's LGBTQ+ history told through landmarks you can visit — plus a self-guided route.
