Part of the Gay Chicago Guide — bars, events & things to do.
Friday, August 21, 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, Jul 18
9 PM - 2 AM
Dorothy, Chicago
Dance party at Dorothy in Chicago celebrating four decades of Top 40 — pop hits spanning 1986 to 2026 with music and live performances on a Sunday night.
Mon, Jul 20
7 PM - 8:30 PM
Dorothy, Chicago
Poetry reading at Dorothy in Chicago celebrating dezireé a. brown's debut collection They/She/He — tender and fierce queer verse on a Tuesday night.
Wed, Jul 22
7 PM - 8:30 PM
Dorothy, Chicago
Intimate WLW songwriter showcase at Dorothy in Chicago — original songs and the personal stories behind each one, performed in a close-knit setting.
Fri, Jul 24
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.
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Your complete guide to LGBTQ+ Chicago — the best gay bars, annual events, neighborhoods, hotels, and things to do in the Windy City.
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