Part of the Gay Chicago Guide — bars, events & things to do.
Friday, July 10, 2026
Get ready for an electric night with Dorothy's Resident DJ Ca$h Era, who brings her masterful open-format mixing and Chicago hip-hop expertise to the decks on the second Friday of every month. With over a decade of professional experience and a title as Chicago's Best Hip-Hop DJ, Ca$h Era knows how to keep the dance floor moving and the energy high in Dorothy's sexy, subterranean speakeasy. Expect four hours of expertly curated beats that'll have you dancing until 1am—just $10 to get in and join the community that makes Dorothy one of the country's most iconic lesbian bars. This event was imported by Out x Out. Please visit the venue link to verify details.
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Mon, Jul 27
7 PM - 11 PM
Dorothy, Chicago
Sapphic Serenade: monthly queer karaoke hosted by E at Dorothy's underground lounge. Final Monday of each month. Community, laughter, and live performances.
Thu, Jul 30
7 PM - 8:30 PM
Dorothy, Chicago
Rhinestone Microphone is a queer open mic night at Dorothy in Chicago where performers take the stage before a supportive crowd and a featured act.
Fri, Jul 31
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 2
7 PM - 8:30 PM
Dorothy, Chicago
You Are Here is a variety-show fundraiser at Dorothy in Chicago, with the cast raising money for their newest production over a night of performances.
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