Part of the Gay Chicago Guide — bars, events & things to do.
Friday, August 7, 2026
Dorothy Debuts is a cover-free night of music featuring two DJs, La Hechicera and Angelgirl Eva, who have never played the lesbian bar before.
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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.
Wed, Aug 26
6 PM - 11 PM
Dorothy, Chicago
IRL is a no-cover singles mixer at Dorothy in Chicago, an unstructured evening for LGBTQ+ singles to meet in person rather than on an app.
Thu, Aug 27
7 PM - 8:30 PM
Dorothy, Chicago
Rhinestone Microphone, Dorothy's queer open mic hosted by Twinka Masala, returns Aug 27 with ten performers spanning comedy, music, and drag.
Fri, Aug 28
9 PM - 1 AM
Dorothy, Chicago
Monthly Latin dance night with DJ Jenny Fox at Dorothy, Chicago's underground lesbian cocktail lounge. Every Friday with all Latin music and queer community vibes.
MonthlySun, Aug 30
7 PM - 8:30 PM
Dorothy, Chicago
The Bi Wives Club comedy showcase returns to Dorothy Aug 30 with a stacked lineup of queer Chicago comics — ASL interpretation included.
Let people know you're going, see who else is attending, and share the event with friends.
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