Chicago House TransSafe Drop In

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.

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.

Monday nights at Dorothy just got better — a rotating lineup of queer films that actually spark conversation, watched with people who get it. This week it's STICK IT, the cult classic about a rebellious gymnast that's become a queer favorite for all the right reasons. Grab a drink in the subterranean speakeasy atmosphere, settle in with your chosen family, and experience the kind of community moment that makes you remember why you love this place.

Monday night trivia at 2Bears Tavern Uptown is the kind of low-key, reliably fun thing that keeps regulars coming back. Show up with a team, test your knowledge, grab a cheap drink, and enjoy the kind of crowd that actually knows how to have a good time without taking themselves too seriously.

Kick off the week with Sidetrack's legendary Show Tunes night — a room full of people who know every word, a DJ spinning Broadway hits and pop classics, and the kind of sing-along energy that makes Monday feel like a celebration. Eight hours of pure joy, starting at 8pm.