Chicago House TransSafe Drop In

Sunroom, a Chicago-based vocal trio, brings an evening of folk and soul harmony to Dorothy's intimate underground space. Expect original compositions and thoughtfully arranged covers that showcase the kind of vocal interplay that makes you lean in and listen. Perfect for a Wednesday night when you want something genuine and unhurried.

Drag bingo night where the glamour is as much a part of the game as the numbers. Hosted in an intimate setting with rotating performers calling the balls, sharp banter, and the kind of crowd that actually knows how to have fun. Wednesdays at 7pm — free to play, drinks on you.

Wednesday nights at the SoFo Tap belong to the bears who show up for trivia, prizes, and the kind of crowd that actually knows their stuff. Hosted by Beartender Thomas, this is trivia night for people who geek out — expect questions that hit different, 1st/2nd/3rd place prizes, and new raffles running weekly. Show up, test your brain, and hang with your people.

An evening celebrating Broadway's best with strong drinks and good company. Whether you're a musical theater devotee or just looking for a fun midweek escape, this is the kind of event that reminds you why show tunes hit different in a room full of people who get it.

Wednesday night karaoke at Jackhammer means a room full of people who actually know how to have fun with a mic — no judgment, just good vibes and whatever song you've been dying to belt. The kind of crowd that cheers you on whether you're nailing it or hilariously bombing it. Cheap drinks and a solid sound system make it easy to keep coming back.

Lady Gaga takes over Sidetrack on the third Wednesday of every month—a night built entirely around her music videos and the dance floor that comes alive when her catalog hits the screens. Expect the crowd to know every word, every beat, and exactly when to lose it. 9pm-2am.