Part of the Gay Chicago Guide — bars, events & things to do.
Friday, July 17, 2026
Join us for Sapphic Serenade: Friday Night Feelings, our monthly queer karaoke night hosted by E! Grab the mic and belt out your favorite songs in a room full of queer women, trans folks, and allies in Dorothy's intimate 1970s-inspired lounge. Whether you're belting ballads or screaming anthems, expect a night that starts conversational and builds into pure joy—the perfect blend of date-night cocktails and uninhibited fun. This event was imported by Out x Out. Please visit the venue link to verify details.
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Mon, Jun 22
7 PM - 9 PM
Dorothy, Chicago
Monthly gay film screening at Dorothy lesbian speakeasy. Watch She's The Man with craft cocktails and community. Hosted by Shelli Nicole.
Tue, Jun 23
7 PM - 8:30 PM
Dorothy, Chicago
Queer open mic night hosted by Twinka Masala at Dorothy in Chicago. Weekly Tuesday performances in an intimate speakeasy with glamorous, authentic queer voices.
Wed, Jun 24
7 PM - 9 PM
Dorothy, Chicago
Watch Billie Eilish's Hit Me Hard and Soft tour film in Dorothy's plush conversation pits. Intimate screening in Chicago's subterranean gay speakeasy.
Thu, Jun 25
7 PM - 8:30 PM
Dorothy, Chicago
Live queer country music at Dorothy's subterranean speakeasy. #QueerCountry Bandwagon & Kelsey Montanez perform Thursdays. $12 advance, $17 door.
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