Pop! x Strapped!

Drag Shows

Six local drag artists performing two numbers each that bring them genuine joy — whether it's a long-time favorite or a debut they can't wait to share. Produced by Ryder Knight, Chicago's sluttiest glam rockstar and trans drag king, this is an evening built around watching performers in their absolute element. Doors at 6pm, show at 7pm. $12 in advance, $17 at the door.

Movie Night

Shelli Nicole hosts the monthly screening series that gives queer films the bar night they deserve. This month: Teenage Sex and Death at Camp Miasma. Doors open at 6pm for happy hour, screening starts at 7pm, and there's an intermission with prizes from local spots and chances to win free drinks at sister bar Fathom. Captions included. Free, 21+.

Social Events

Set intentions, pick a flower that matches what you're looking for—casual, long-term, or friends first—and see if sparks fly. This sapphic social at Dorothy pairs in-person connection with a dedicated Tinder profile so you can keep the conversation going after the night ends. Free entry, professional photos, drinks, and a room full of women actually looking to meet someone. Red, white, or black encouraged.

Comedy

Slugface Productions brings their brand of vicious, absurd comedy back to Dorothy with seven alternative comedians ready to bare their teeth. Maison Monroe, Femme De Violette, Devin Jeong Wright, Madeleine Libman, Natalie Freisinger, Taylor Meredith, and Kristi Durkin take the stage for a night of cutting standup that doesn't pull punches. Doors at 6pm, show at 7pm; $12 in advance, $17 at the door.

burlesque

The Velvet Vixens and a killer lineup of Chicago burlesque performers are bringing Halloween heat to Dorothy—think fierce femmes, spooky seduction, and a certain Rocky Horror tradition creeping out of the shadows. Doors at 6pm, show at 7pm. $20 general admission ($25 at the door), $25 for VIP Bed Lounge seating.

Dance Party

Halloween is for the sapphic singles — and this party proves it. Costumes are mandatory, the DJ is spinning, and there's a costume contest with a real prize waiting. Spooky icebreaker games, a confessional booth for making out, and drink specials for singles only round out the night. The vibe is pure chaos in the best way: show up solo, invite your dating app matches if you're feeling it, and spend the evening flirting and being the most chaotic version of yourself. Tickets start at $15 for general admission, with group and match pass discounts available.