Part of the Gay Chicago Guide — bars, events & things to do.
Chicago, Illinois
A subterranean lesbian cocktail speakeasy behind an unmarked red door.
Dorothy is a below-ground lesbian cocktail lounge on Chicago Avenue in West Town, reached through an unmarked red door — no sign, just the painted "2500" and a staircase down into a 1970s-inspired room of plush seating and low light. It opened on Valentine's Day 2020, weathered repeated COVID closures, and fully reopened in July 2022 under married owners Zoe Schor and Whitney LaMora, whose Friends of Dorothy group is built specifically around queer gathering spaces. It's one of only a few dozen lesbian bars left in the country, which makes it both a neighborhood living room and a destination worth crossing town for. The crowd is queer women and their friends, and the energy runs conversational early, louder late — closer to a date-night cocktail bar than a club. Expect a rotating calendar rather than a single signature night: karaoke, open mics, live music, gender-expansive Enby nights, immersive theater and storytelling all cycle through.
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