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

Saturday, July 4, 2026
Join us for Independence Day at Chicago's only lesbian bar—we're celebrating by staying open and ready to welcome you into our below-ground sanctuary. Whether you're looking for a laid-back evening of cocktails and conversation or planning to stay late as the energy picks up, Dorothy is the place to be. Bring your friends, settle into the plush seating, and toast to community, freedom, and queer joy. This event was imported by Out x Out. Please visit the venue link to verify details.
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Mon, Jun 22
7 PM - 9 PM
Dorothy, Chicago
Monthly gay film screening at Dorothy lesbian speakeasy. Watch She's The Man with craft cocktails and community. Hosted by Shelli Nicole.

Tue, Jun 23
7 PM - 8:30 PM
Dorothy, Chicago
Queer open mic night hosted by Twinka Masala at Dorothy in Chicago. Weekly Tuesday performances in an intimate speakeasy with glamorous, authentic queer voices.

Wed, Jun 24
7 PM - 9 PM
Dorothy, Chicago
Watch Billie Eilish's Hit Me Hard and Soft tour film in Dorothy's plush conversation pits. Intimate screening in Chicago's subterranean gay speakeasy.

Thu, Jun 25
7 PM - 8:30 PM
Dorothy, Chicago
Live queer country music at Dorothy's subterranean speakeasy. #QueerCountry Bandwagon & Kelsey Montanez perform Thursdays. $12 advance, $17 door.
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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.
