126 bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
Step into River North's 18,000-square-foot prohibition-era fantasy at Untitled Supper Club, where weekly cabaret and live music fill the lavishly designed space. They're also sitting on one of the world's largest American whiskey collections — so yeah, you're staying for a drink.
V Live Chicago delivers high-energy performances ranging from Latin bands to DJ sets in a nightclub built for the musically inclined. When the lineup hits, this venue packs real heat and keeps the dance floor moving all night.
The International Festival of Life takes over Washington Park on the South Side with live music, global food vendors, and cultural performances from around the world. It's a sprawling celebration of diversity and one of the best free summer festivals in the city.
Do Division Street Fest is Wicker Park's annual block party throwdown with live music, local vendors, and the kind of neighborhood energy that spills across every corner of Division Street. It's one of the best free street fests on the North Side.
Cozy 100-seat listening room in Streeterville. Performances six nights a week. Straight-ahead jazz, traditional, gypsy jazz, big band, and New Orleans-style.
# Woodlawn Tap The Tapper is Hyde Park's gritty institution—a cash-only dive where $3 Millers flow freely and the jukebox never stops spinning jazz and blues, especially on Sunday nights when locals pack in shoulder-to-shoulder. Grab a Chicago-style hot dog and settle in until 2am with the kind of crowd that's been coming here since before most bars had Instagram accounts. This is where the neighborhood's real soul lives.