Post Brunch Fun

Daddy Disco is back for a Saturday afternoon tea dance at Sidetrack — dance hits from the 80s, 90s, and 2000s with hosts Michael and Jeremy keeping the energy up. It's the kind of daytime dance party that hits different, with a crowd that knows how to have a good time and a sound system that makes you remember why you love these songs.

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.

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.

Sidetrack's annual Halloween costume edition of Dog Day is a puppy-loving afternoon with a parade of costumes, games, and all the fun the community brings. Running 1-5pm with festivities ramping up around 3pm, it's the kind of Saturday that celebrates what makes this crew special.