Part of the Gay Chicago Guide — bars, events & things to do.
Monday, August 31, 2026
Sapphic Serenade is Dorothy's Monday karaoke night hosted by E., kicking off with the Monday Musicals power hour. Doors open at 6pm with karaoke sign-ups, and the mic stays warm from the 7pm power hour until last call.
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Fri, Aug 7
9 PM - 1 AM
Dorothy, Chicago
Dorothy Debuts at Dorothy, Chicago's lesbian bar, is a cover-free night with DJs La Hechicera and Angelgirl Eva making their venue debut.
Sat, Aug 8
9 PM - 1 AM
Dorothy, Chicago
DJ Feature brings Chicago's own MobeeThicc to Dorothy for a late night of music at the neighborhood lesbian bar, spinning from nine into the early hours.
Sun, Aug 9
6 PM - 11 PM
Dorothy, Chicago
Silent Book Club at Dorothy in Chicago, with Chicago Public Library, is a chance to gather in quiet camaraderie and read without book-club pressure.
Wed, Aug 12
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.
MonthlyThu, Aug 13
7 PM - 8:30 PM
Dorothy, Chicago
Nervous Laughter is a monthly comedy night at Dorothy in Chicago, celebrating the nervous, delightfully weird corner of stand-up comedy.
Fri, Aug 14
10 PM - 2 AM
Dorothy, Chicago
Monthly queer karaoke night for women, trans folks, and allies. Sing, drink, and celebrate at Dorothy's 1970s lounge in Chicago.
MonthlyLet people know you're going, see who else is attending, and share the event with friends.
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