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

Sunday, June 28, 2026
Grab the mic and show off your pipes at Starlight Karaoke, hosted by the fabulous Sutton Fister every Sunday! Whether you're belting out country classics, pop anthems, or your guilty pleasure bops, this is your moment to shine in a room full of cheering queens, cowboys, and everyone in between. It's the perfect blend of Charlie's signature sass and Southern charm—come ready to sing, laugh, and celebrate with your people. This event was imported by Out x Out. Please visit the venue link to verify details.
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Sat, Jun 27
11 PM - 4 AM
Charlie's, Chicago
Weekly Saturday drag show at Charlie's Chicago featuring Bella DeBalle, Pixel, and Persephone Brooklyn with DJ Lightning LuLu. Late-night dance party.
Weekly
Sun, Jun 28
5 PM - 7 PM
Charlie's, Chicago
Monthly drag showcase every Sunday at Charlie's Chicago. Hosted by PB, featuring live performances and queer nightlife in a rodeo-themed venue.
Monthly
Sun, Jun 28
11 PM - 4 AM
Charlie's, Chicago
Weekly Latin dance party at Charlie's Chicago hosted by Persephone Brooklyn LaRue and Luna LaCatrina. DJ X-tasy spins every Sunday night.
Weekly
Sun, Jun 28
11 PM - 4 AM
Charlie's, Chicago
Weekly Latin dance party at Charlie's Chicago. DJ X-tasy, hosted by Persephone Brooklyn LaRue and Luna LaCatrina. High-energy vibes every Sunday.
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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.
