Kit Kat Club Cabaret

Every Monday, trans folks can stop by for free, judgment-free support — housing navigation, employment services, medical referrals, and more. Chicago House has been showing up for the trans community for decades. This is the kind of practical, no-strings help that actually changes things.

Shake off the week's rough start with 90s and 00s music videos, $5 drinks, and a room full of people who get it. Hosted by Danny, this weekly Monday night hangout runs 5pm–2am at SoFo Tap — the perfect excuse to log off and let loose when you need it most.

A weekly gathering for people exploring or questioning their gender identity and expression — a space to connect with others who get it, share experiences, and find community. Whether you're early in your journey or further along, this is a judgment-free place to be yourself.

Monday nights at Center on Halsted belong to recreational volleyball players who know the basics and want to actually play. No competitive pressure, no gatekeeping — just people who get the general rules and want to improve their game in a welcoming environment. Show up ready to move.

An evening of Les Misérables favorites performed cabaret-style at Sidetrack. This theatrical celebration brings the beloved musical to life with intimate arrangements and passionate performances that'll have you singing along. Monday nights at Sidetrack mean show tunes, community, and the kind of entertainment that reminds you why this place is legendary.

Roscoe's is crowning Chicago's best this year, and the competition is the real draw — watching the city's most talented drag performers bring everything they've got to the stage in one night. It's the kind of show where you're on your feet, the energy is electric, and you actually care who wins because you've just watched them prove why they deserve it. May 18th at 7pm is when the community gathers to celebrate the performers who've made Chicago's drag scene what it is.