Part of the Gay Chicago Guide — bars, events & things to do.
Sunday, September 13, 2026
Silent Book Club is Dorothy's monthly gathering for readers who want the company without the assignment - bring whatever you are reading and read together. Entry is always free. This edition is joined by Sheep Cult Comics, an indie comic and bookstore in Wicker Park, who will bring comics and merch to sell.
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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.
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.
Let people know you're going, see who else is attending, and share the event with friends.
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