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

Tuesday, June 23, 2026
Put your trivia skills to the test at Sidetrack's special Heated Rivalry Edition, hosted by Stew. Whether you're a pop culture expert or just here for the competitive energy and frozen cocktails, this themed night brings the heat to the Main Bar and beyond. No cover, no pretense — just good vibes, tough questions, and the chance to prove you know your stuff. This event was imported by Out x Out. Please visit the venue link to verify details.
Have feedback on this description? Let us knowLet people know you're going, see who else is attending, and share the event with friends.

Mon, Jun 22
8 PM - 2 AM
Sidetrack, Chicago
Weekly show tunes night at Sidetrack in Chicago. Sing along to Broadway hits, dance, and enjoy frozen cocktails with the LGBTQ+ community.
Weekly
Wed, Jun 24
9 PM - 2 AM
Sidetrack, Chicago
Monthly Wednesday night dance party at Sidetrack featuring Dua Lipa and Ariana Grande hits. Gay video dance party in Chicago's welcoming venue.
Monthly
Thu, Jun 25
9 PM - 2 AM
Sidetrack, Chicago
Weekly K-Pop night at Sidetrack's gay bars in Chicago. Dance to K-Pop videos and performances with the LGBTQIA+ community every Thursday.

Fri, Jun 26
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.

It's Chicago Pride weekend. The 55th Pride Parade rolls down Halsted on Sunday under the “Free to Be Proud” banner, and we mapped 78 events to get you there — Pride power hours at Scarlet, a Men's Room glow party at Sidetrack, drag brunches at Roscoe's and Kit Kat, and parade-day parties up and down Boystown.

A neighborhood-by-neighborhood map of gay and gay-friendly Chicago — the vibe, the bars, and what it's actually like to live in each, from Boystown to the South Side.
