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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Sat, Jul 11
9 PM - 2 AM
Dorothy, Chicago
Sapphic goth night in Chicago at Dorothy. Moody music, dancing, and queer community in an intimate space. Saturdays.

Sun, Jul 12
6 PM - 11 PM
Dorothy, Chicago
Silent Book Club at Dorothy, Chicago's lesbian lounge, is a monthly quiet reading gathering, this edition featuring Proud City by Block Club Chicago.

Mon, Jul 13
7 PM - 9:30 PM
Dorothy, Chicago
Sing-along screening of Chicago (2002) at Dorothy in Chicago — Queen Latifah trivia at intermission and raffle prizes make this a full Queer Movie Monday night out.

Wed, Jul 15
7 PM - 8:30 PM
Dorothy, Chicago
Weekly vocal trio performing original music and folk-soul covers at Dorothy. Intimate Wednesday evenings of harmony singing in Chicago's gay nightlife scene.
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