Part of the Gay Chicago Guide — bars, events & things to do.
Friday, August 14, 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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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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