BARK BARK BITE: A Night of Cutting Standup Comedy

Gyrate is a Black, Latine, and Queer-run party that celebrates Caribbean culture and the Black Diaspora. Their Dorothy debut lands right in Pride season—expect a dance floor that knows how to move, music that hits different, and a room full of people who get it.

Dorothy's closing its doors Sunday evening so the whole crew can hit the streets for Chicago's Pride Parade—because some things are bigger than the bar. Come find us in the march, then stick around for the celebration that follows. It's the kind of community moment that reminds you why this place matters.

The queer karaoke night that actually gets it — a room full of sapphic energy, hosted by E., closing out Pride season at Dorothy. Expect singalongs, cheers, and the kind of crowd that knows every word to every song that matters. Monday nights at Dorothy just got a lot more fun.

Two DJs making their Dorothy debut spin the night at this underground lesbian bar favorite. Cover-free entry means you can show up, dance, and see what happens when fresh talent hits the decks in this intimate West Town speakeasy. Friday night energy, no cover charge — exactly the kind of low-key discovery that keeps the neighborhood coming back.

Dorothy's keeping the lights on and the drinks flowing for Independence Day — a rare summer holiday opening for the West Town speakeasy. Come celebrate with the community in that intimate, retro-cool underground space that's become a favorite for everyone who knows about it.

Venus brings tarot readings infused with mediumship and spell work to Dorothy's underground speakeasy. An intimate evening for anyone curious about divination, energy work, or just looking for a different kind of magic on a Wednesday night. 6-10pm.