Part of the Gay Chicago Guide — bars, events & things to do.

Saturday, June 13, 2026
Grab the mic and celebrate sapphic joy at Sapphic Serenade, Dorothy's Saturday Night Special karaoke night hosted by E—and it's completely free to get in! Whether you're belting out your favorite power ballad or cheering on friends, expect the electric, inclusive energy that makes Dorothy a queer cultural institution. Come as you are and sing your heart out in this sexy subterranean speakeasy where every "friend of Dorothy" belongs. This event was imported by Out x Out. Please visit the venue link to verify details.
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Fri, Jul 17
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.
Monthly
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.
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