Slaycation: A Travel Themed Drag Show

The circus rolls into Dorothy for a night of pure spectacle — puppetry, buffoonery, sex appeal, and just enough delightful chaos to keep things interesting. This is the kind of event that reminds you why you love this community: weird, bold, unapologetically fun, and designed for everyone who's ever wanted to see a lesbian circus.

Two queer musicians, one intimate night underground. Brooklyn's Your Friend Rachel brings her distinctive sound to Dorothy's subterranean stage, sharing the bill with Chicago's The God Awful Small Affairs. Live music for people who actually listen — expect the kind of performance that reminds you why you showed up in the first place.

A fun and flirty show built for queers finding their people later in life. If you're looking to make real connections with other late bloomers in the community, this is your night — expect good energy, genuine conversations, and the kind of vibe where everyone's actually here for the same reason.

No frills, no fuss, no cover—just a night to gather if you're queer, single, and ready to mingle. Dorothy's subterranean speakeasy becomes the spot where you can actually talk to people without screaming over a DJ, shoot your shot, and maybe meet someone worth knowing. Wednesday at 6pm means you catch the early crowd before things get late.

Rhinestone Microphone is a monthly queer open mic celebrating all forms of performance — 10 local performers get five minutes to share what they do best in front of an enthusiastic crowd, with priority given to BIPOC and first-time performers. The night opens with open mic and closes with award-winning burlesque performer Harlem Nyte. Doors at 6pm, show starts at 7pm. $8 in advance, $12 at the door.

Jenny Fox, Chicago's Puerto Rican Princess, takes over Dorothy's basement for a night of pure perreo, cumbiatón, salsa, merengue, and más. Doors at 6pm, Jenny spins from 9pm to 1am—come ready to dance and romperla. $10 cover at the door; Dorothy stays open until 2am.