Part of the Gay Chicago Guide — bars, events & things to do.
Wednesday, August 19, 2026
Slaycation is a new travel-themed drag show at Dorothy where each performer whisks the audience away to a dream destination. Expect passports stamped, looks served, and a full itinerary of drag from Chicago performers in the downstairs lounge.
Have feedback on this description? Let us knowDrag brunches, circuit nights & every party worth knowing in Chicago — in your inbox every week.
Thu, Sep 17
7 PM - 8:30 PM
Dorothy, Chicago
Life is a Queer Cabaret — a queer cabaret and variety show at Dorothy in Chicago's West Town.
Fri, Sep 18
10 PM - 2 AM
Dorothy, Chicago
Monthly queer karaoke night for women, trans folks, and allies. Sing, drink, and celebrate at Dorothy's 1970s lounge in Chicago.
MonthlyLet people know you're going, see who else is attending, and share the event with friends.
Your complete guide to LGBTQ+ Chicago — the best gay bars, annual events, neighborhoods, hotels, and things to do in the Windy City.
Robbie S.
Everything you need for Chicago's Haunted Halsted Halloween Parade — the route, the costume contest, the Northalsted bars that go all out, and where to stay that's gay.
Robbie S.
Parvati Shallow's Survivor brunch, Queen! celebrates Lucy's birthday, and G.E.M. turns five at Jackhammer — plus 92 ways to fill your weekend.
Robbie S.
A citywide guide to the best gay bars and clubs in Chicago — Northalsted's neon-lit video bars, Andersonville's laid-back locals, historic South Side spots and everything between.
Robbie S.
Laid-back patios, karaoke, and the least pretentious crowd in the city — here's where Chicago's bears, cubs, and otters actually hang out, night by night.
Robbie S.
From cruise bars in Rogers Park to the Chicago Eagle, here's every corner of Chicago's leather and kink scene — the birthplace of IML.
Robbie S.