Monthly Dog Day

Pink Pony Club brings the heat to Sidetrack with a themed party that celebrates queer nightlife at its most fun and unapologetic. Expect a packed dance floor, high energy, and a crowd ready to dance all night.

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.

Kick off your weekend at Sidetrack's legendary Friday show tunes sing-along! Every other Friday, the rooftop and video bar come alive with a crowd that knows every word to their favorite Broadway classics and pop standards. Grab a drink, catch the sunset, and get ready to belt out the hits with fellow show tune lovers in the kind of communal, joyful singing that makes this Chicago tradition legendary.

Sidetrack's Friday nights are built for dancing — a packed dance floor, high-energy DJ sets, and a crowd that knows how to make the most of the weekend. It's the kind of night that reminds you why this place is a Chicago institution.

Sidetrack's monthly pup playdate is exactly what it sounds like — a chance to bring your four-legged friend out for a few hours of socializing, treats, and good vibes. The first Saturday of each month from 1-5pm, this dog-friendly afternoon draws a crowd of queer folks and their furry companions. Tito's Handmade Vodka usually shows up with doggy swag to hand out, and the whole vibe is relaxed, inclusive, and genuinely fun for everyone (two-legged and four-legged alike).

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.