Part of the Gay Chicago Guide — bars, events & things to do.
Friday, September 18, 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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Sat, Aug 15
9 PM - 2 AM
Dorothy, Chicago
Dorothy Pop! Songs of the Summer is a pop dance party at Chicago's lesbian bar, with DJ sets, live performances and a late floor.
Sun, Aug 16
6:30 PM - 8:30 PM
Dorothy, Chicago
Masala Dykes is a South Asian centered sapphic meet-up at Dorothy in Chicago, a relaxed early-evening community night built for making connections.
Mon, Aug 17
7 PM - 9:30 PM
Dorothy, Chicago
Host Shelli Nicole screens John Tucker Must Die at Dorothy in Chicago, the August edition of the bar's third-Monday movie night, with prizes.
Tue, Aug 18
7 PM - 8:30 PM
Dorothy, Chicago
Adrianne Blanks celebrates her birthday at Dorothy in Chicago with a one-night bill of live music and performances from friends.
Wed, Aug 19
7 PM - 8:30 PM
Dorothy, Chicago
Slaycation brings a travel-themed drag show to Dorothy in Chicago on Aug 19 — each queen transports the room to a different dream destination.
Thu, Aug 20
6 PM - 11 PM
Dorothy, Chicago
Bartender Lou hosts Trans/Enby Night at Dorothy in Chicago, centering trans and non-binary folks, with DIY for Gaza and Vyle Studios.
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