Trans Fall Festival

Dance Party

Sidetrack

Kick off your weekend at Sidetrack in Chicago's Lakeview neighborhood with Friday Afternoon Show Tunes, where the whole room sings along to the classics from 4-9pm. Doors open at 3pm, and when the sing-along wraps up, you can stick around for the Friday Night Dance Party.

Drag Shows

Kit Kat Club

Rocky Horror meets drag at Kit Kat Club's themed dinner show featuring the world-famous Kit Kat Divas in full costume spectacle. Your ticket includes a prix fixe menu with starter, choice of entree, and two martinis, plus two hours of pumping music, personal interaction with the divas, and high-energy performances. This is the kind of night that lives in your memory.

Dance Party

Dorothy

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.

Trivia

2Bears Tavern Uptown

High-energy drag trivia night hosted by Tia Pet at 2Bears Tavern Uptown. The questions are tricky, the host is shady, and the room is completely out of control—in the best way. Gather your team and test your wits over three hours of comedy, competition, and chaos. Free to play, no cover, drinks flowing, and the perfect way to kick off a Friday night at this neighborhood bar. Every Friday from 7pm to 10pm.

fetish

Jackhammer

The fourth Friday of every month, Jackhammer turns its floor over to leather, rubber, harnesses, hoods, and everything in between. Whether you're building a collection or wearing your first piece, this 9PM to 4AM night is about showing up, exploring, and getting into the energy of a packed room of people who understand the assignment. Entry is free before 10PM, and dressing to the theme is strongly encouraged.

competition

Hydrate Nightclub

Freshman 15 is a weekly drag competition that turns up the heat every Friday night at Hydrate. With the finale approaching, the pressure's on for a thrilling showcase of local talent under the direction of Headmistress Bambi Banks and faculty Starr Banks and Neutral Gena. DJ Geo Diamond and VJ George G keep the energy locked in. $5 cover, 9 PM to 11 PM.