Part of the Gay Chicago Guide — bars, events & things to do.
Friday, May 8, 2026
Dance the night away with Dorothy's resident DJ Ca$h Era, spinning every second Friday of the month at this iconic lesbian cocktail lounge. Expect expertly curated beats in an intimate, electric atmosphere—the perfect vibe to enjoy craft cocktails and connect with the community. $10 cover gets you in the door for a night of pure queer joy. This event was imported by Out x Out. Please visit the venue link to verify details.
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Tue, Jun 16
6 PM - 11 PM
Dorothy, Chicago
Join Bartender Lou for trans and non-binary celebration at Dorothy speakeasy. Shop local queer vendors, connect with community every Tuesday.
Wed, Jun 17
7 PM - 8:30 PM
Dorothy, Chicago
Queer comedy showcase at Dorothy featuring Chicago's comics. ASL interpreted, every Wednesday. Gay nightlife in Chicago's underground venue.
Thu, Jun 18
7 PM - 8:30 PM
Dorothy, Chicago
Queer cabaret featuring QPOC artists at Dorothy's speakeasy. Musical theatre, storytelling, and community every Thursday in Chicago.
Fri, Jun 19
6 PM - 1 AM
Dorothy, Chicago
DJ Cut-Cuz spins a Juneteenth celebration at Dorothy, Chicago's lesbian bar. No cover, cocktails, and all-night dancing in an intimate speakeasy.
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