Chaotic Singles: Sapphic Halloween Party

A vibey, nostalgic sketch comedy show that feels like Sesame Street but queerer and for adults. Follow Todd the Gig Worker as he faces some truly bizarre challenges—like potentially losing his eyeballs to Sentient Gutter Sludge—with help from his found family of friends. Hosted by Our Lady of Dough with special guest Todd Douglas. Doors at 6pm, show at 7pm. $12 in advance, $17 at the door.

Reclaim homecoming on your own terms—dress how you want, bring who you want, and dance till 2am. The Chicago Spirit Brigade opens the night with cheer activations, then DJ Syd takes over the dance floor at 10pm before DJ DaiGroovie keeps the party rolling through midnight. $10 cover, 21+, all night long.

Roz Hernandez brings her chart-topping queer paranormal comedy podcast to life for one night only—and she's turning it into a ghost story competition. Bring your best real paranormal tale (3 minutes or less) for a shot at winning merch, or just come to hear the spookiest stories from the crowd. Everyone gets a free meet and greet with Roz after the show, plus exclusive merch available for purchase. No recording, but photos are encouraged.

Two DJs making their Dorothy debut spin back-to-back for a cover-free night in the subterranean lounge. DJ th3m opens with early 2000s nostalgia and bass-heavy rap (9-11pm), then Naughty G takes over with house, reggaeton, electronic, and hip hop until 1am. No cover all night, doors at 6pm, dancefloor kicks off at 9pm.

Fang & Fae brings their permanent jewelry magic to Dorothy for an evening of custom-fitted chains, charms, and adornment. Build your own piece — choose from a curated collection and walk out with something uniquely yours, welded seamlessly and designed to be lived in and layered over time. Solo or with friends, walk-ups welcome all night. Happy hour runs 6–7pm; Dorothy stays open until 11pm.

Roz Hernandez brings her chart-topping queer paranormal comedy podcast to the stage for a second sold-out show — and this time, the audience gets to compete. Bring your best real ghost story (3 minutes or less) for a chance to win merch, or just come to hear everyone else's spooky tales. Either way, you're getting a meet-and-greet with Roz after the show and an evening of genuinely fun, queer-centered paranormal chaos.