Saturday Afternoon at Sidetrack

Friday afternoons at Sidetrack belong to Show Tunes — a 3-7pm sing-along that's part celebration, part therapy, and entirely unironic. The kind of event where belting out Sondheim with strangers becomes a genuine good time, and the crowd gets louder with every drink. It's what a neighborhood bar does best: give people a reason to show up early and stay late.

Friday nights at Sidetrack belong to All Stars — the show that brings back the queens you already love and reminds you why they earned their place in the competition. Screenings run 7-9pm, which means plenty of time to grab a drink, settle in with the crowd, and lose it when your favorites hit the runway.

Sidetrack's Friday night is the rooftop's moment to shine — the space opens early evening and keeps the energy high until 2am with dancing, DJ sets, and a crowd that knows how to make the most of a night out. It's the kind of reliable weekly ritual that becomes the centerpiece of your weekend plans.

Sidetrack's Pride Fest takes over the rooftop for a full afternoon of celebration. Meet Real Housewives and Traitors star Candiace Dillard Bassett at a free meet & greet from 2-5pm, then stick around for drag performances and a chance to get on stage with Boy J and Veronica Pop from 3-6pm. Win prizes, soak up the sun, and be part of the neighborhood's biggest Pride weekend moment.

Saturday rooftop vibes at Sidetrack with DJ kleedisme spinning the soundtrack. This is the kind of afternoon that turns into evening — good weather, good drinks, and a crowd that knows how to have a genuinely good time without taking itself too seriously. Expect dancing, sunshine, and the rooftop energy that makes summer in Chicago actually worth the wait.

Sidetrack's Saturday night institution — a packed dance floor, rotating DJs, and the kind of crowd that knows how to keep the energy going until 3am. This is where the weekend really happens.