Part of the Gay Chicago Guide — bars, events & things to do.
Monday, June 29, 2026
Grab the mic and show off your vocal talents at Dorothy's monthly karaoke night, hosted by the venue's own bartender E. This is your chance to belt out your favorite songs in an intimate, sexy speakeasy setting where every "friend of Dorothy" is celebrated. Whether you're a karaoke veteran or stepping up to the mic for the first time, expect a fun, supportive crowd ready to cheer you on in one of the country's most beloved lesbian bars. This event was imported by Out x Out. Please visit the venue link to verify details.
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Sat, Jun 27
9 PM - 1 AM
Dorothy, Chicago
Gyrate brings Black, Latine, and queer celebration to Dorothy every Saturday. High-energy Caribbean and Black Diaspora dancing in Chicago's lesbian cocktail bar.
Fri, Jul 3
9 PM - 1 AM
Dorothy, Chicago
Cover-free Friday night at Dorothy Chicago featuring DJs Cobra B and Queen Méabh. DJ sets 9pm–1am. New talent, no cover charge.
Sat, Jul 4
6 PM - 2 AM
Dorothy, Chicago
Join us for Independence Day at Dorothy, Chicago's lesbian bar. Cocktails, community, and queer joy in our below-ground sanctuary.
Wed, Jul 8
6 PM - 10 PM
Dorothy, Chicago
Monthly Wednesday tarot readings with mediumship and spell work at Dorothy, Chicago's lesbian bar. Candlelit pop-up with cocktails and community.
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