Part of the Gay Chicago Guide — bars, events & things to do.
Wednesday, August 19, 2026
Steppenwolf 1700 Theater, Chicago
1700 N Halsted St, Chicago, IL 60614, United StatesAn old-school-style cabaret from Chicago performer Carl Chadek, built from Broadway, the Great American Songbook, classic pop, and just maybe a little comedy. Think dinner jackets, evening gowns, and martinis, with the title nodding to the audition-room sting of being told you're "not right for that." An evolution of the act he first staged at Davenport's Piano Bar, now a one-night turn in Steppenwolf's LookOut series at the intimate 1700 Theater.
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Thu, Aug 13
6 PM - 9 PM
Kit Kat Lounge, Chicago
Weekly drag dinner theater in Chicago's Northalsted. Haute couture performances, $10 martinis, and upscale dining in an Art Deco room every Thursday.
Weekly
Thu, 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.
Thu, Aug 13
7 PM - 9 PM
Replay Lakeview, Chicago
Thirsty Thursday Trivia at Replay Lakeview, Chicago: weekly Thursday trivia at 7pm with cash prizes in the Halsted Street bar-arcade.
Weekly
Thu, Aug 13
7 PM - 9 PM
Nobody's Darling, Chicago
Monthly queer matchmaking at Nobody's Darling. Friends pitch 35+ singles via slide deck—no apps, just community, mingling, and real connections.
Thu, Aug 13
8 PM - 10:30 PM
The Vic Theatre, Chicago
Drag Race's Bosco brings The Marvelous Miss Gender tour to The Vic Theatre, Chicago, Aug 13.
Thu, Aug 13
8 PM - 2 AM
Cell Block, Chicago
Weekly drink specials at Cell Block, Chicago's leather and fetish bar. Front bar open to all, back bar at 8pm for the leather community. Check dress code.
WeeklyLet people know you're going, see who else is attending, and share the event with friends.
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