Sunday Funday After Dark

Sidetrack's legendary Sunday afternoon tradition — the whole room singing along to Broadway classics and pop standards across the Main, Cherry, and North Bars. It's the kind of joyful, communal sing-along that makes strangers harmonize together, with rooftop and video bars packed with people who know every word. A weekly ritual that's become the neighborhood's favorite reason to start the weekend early. Arrive early, bring your voice, and settle in for an afternoon of pure theater magic.

Every Monday, Sidetrack turns into Chicago's ultimate show tunes sing-along. Broadway classics and movie musicals play on the big video screens while a room full of people who know every word belts along together. It's a beloved weekly tradition blending theater-kid energy with dance party vibes — come whenever the mood strikes and stay for the chorus of strangers turned friends.

An evening where LGBTQ+ voices take center stage to share their stories — the kind of intimate, authentic gathering that reminds you why listening matters. Real people, real narratives, real connection.

Stew hosts Sidetrack's weekly trivia night—test your pop culture knowledge against the crowd, then stick around for Pop Favorite Videos spinning until 2am. It's the kind of reliably fun Tuesday that builds a crowd of regulars who actually know their stuff (and aren't afraid to shout the answers).

Sidetrack's weekly Thursday night party takes over the Main, Cherry, and North Bars with high-energy Latin beats, DJ-driven dance floors, and a crowd that knows how to move. Expect a packed dance floor, strong drinks, and great vibes — the go-to Thursday escape for anyone who wants to dance to Latin rhythms without the pretense. Occasional themed editions swap in pop music videos and special guest hosts.

The Saturday afternoon shift at Sidetrack — when brunch hangs on and the dance floor starts calling. Grab a drink, catch up with friends, and ease into the weekend vibe before things really heat up. It's that sweet spot between lazy brunch energy and full-on nightlife, with good music, good people, and a rooftop if you need air.