Part of the Gay Chicago Guide — bars, events & things to do.
Friday, August 28, 2026
Step into Dorothy's underground world for Latin Night, a monthly celebration of Latin music and dance hosted by resident DJ Jenny Fox. Whether you're a seasoned dancer or just here to vibe with the community, expect an electric night of expertly curated beats in the intimate glow of this iconic lesbian speakeasy. Come as you are and dance like nobody's watching — because in this space, you're among friends. This event was imported by Out x Out. Please visit the venue link to verify details.
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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.
Fri, Aug 21
9:30 PM - 1:30 AM
Dorothy, Chicago
Monthly Friday DJ night with Chicago's resident hip-hop DJ Ca$h Era at Dorothy lesbian bar. Open-format mixing, $10 entry, dancing until 1am.
Sat, Aug 22
9 PM - 1 AM
Dorothy, Chicago
DJ Feature brings Chicago-based DJ Love Marie to Dorothy for a late night of music at the neighborhood lesbian bar, running into the early hours.
Mon, Aug 24
7 PM - 8:30 PM
Dorothy, Chicago
Brooklyn's Your Friend Rachel and Chicago's The God Awful Small Affairs play an LGBTQ+ centered live music night at Dorothy.
Tue, Aug 25
7 PM - 8:30 PM
Dorothy, Chicago
Pitch Your Peeps: Late Bloomers is a slide-deck matchmaking show at Dorothy in Chicago, centering LGBTQ+ folks who came into it later in life.
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