Part of the Gay Chicago Guide — bars, events & things to do.
Friday, August 21, 2026
Dorothy's resident DJ Ca$h Era takes over the decks on the second Friday of every month, bringing high-energy beats to the venue's iconic subterranean space. Expect a dynamic dance party in the heart of this beloved lesbian cocktail lounge, where the retro '70s atmosphere meets cutting-edge sound. With a $10 cover charge, it's the perfect excuse to descend behind that unmarked red door and dance with Chicago's vibrant queer community. This event was imported by Out x Out. Please visit the venue link to verify details.
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Tue, Aug 25
7 PM - 8:30 PM
Dorothy, Chicago
Pitch Your Peeps: Late Bloomers is a slide-deck matchmaking show at Dorothy in Chicago, centering LGBTQ+ folks who came into it later in life.
Wed, Aug 26
6 PM - 11 PM
Dorothy, Chicago
IRL is a no-cover singles mixer at Dorothy in Chicago, an unstructured evening for LGBTQ+ singles to meet in person rather than on an app.
Thu, Aug 27
7 PM - 8:30 PM
Dorothy, Chicago
Rhinestone Microphone, Dorothy's queer open mic hosted by Twinka Masala, returns Aug 27 with ten performers spanning comedy, music, and drag.
Fri, Aug 28
9 PM - 1 AM
Dorothy, Chicago
Monthly Latin dance night with DJ Jenny Fox at Dorothy, Chicago's underground lesbian cocktail lounge. Every Friday with all Latin music and queer community vibes.
MonthlySun, Aug 30
7 PM - 8:30 PM
Dorothy, Chicago
The Bi Wives Club comedy showcase returns to Dorothy Aug 30 with a stacked lineup of queer Chicago comics — ASL interpretation included.
Mon, Aug 31
7 PM - 11 PM
Dorothy, Chicago
Sapphic Serenade karaoke night takes over Dorothy Aug 31 — sign-ups at 6pm, Monday Musicals power hour at 7pm, singing until last call.
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