56 bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
West Town’s hidden gem: a sliver-thin space that’s been pouring bold, old-school cocktails since ’95, tucked between Wicker Park’s buzz and the river’s edge. Open late, but never crowded—locals know the wait’s worth it for a drink in a room smaller than your average kitchen.
Inventive cocktails and a friendly, knowledgeable staff make The Press Room one of the West Loop's most respected bars. The menu pushes boundaries without being gimmicky, and the industrial-chic space on Washington Blvd sets the right mood. A cocktail enthusiast's dream spot.
A cocktail bar with a focus on seasonal ingredients and a rustic charm.
Thirteen floors up atop the Robey Hotel at the Wicker Park-Bucktown crossroads, The Up Room delivers panoramic skyline views with seasonal cocktails in an intimate indoor-outdoor setting. Sunset drinks here are a rite of passage on the North Side.
James Beard Award-winning cocktail bar hidden behind an unmarked facade. Seasonal craft cocktails, no-phone policy, and intimate candlelit atmosphere.
The Whistler in Logan Square (west) blends award-winning cocktails with intimate live music and DJ sets in a gallery-space that feels more like a secret club than a bar—stay late on Saturdays when the crowd thins and the vinyl spins till 3am.
A no-frills Pilsen bar with DJs, strong drinks, and the kind of authentic neighborhood atmosphere that gentrification hasn't touched. Water Hole Lounge is where locals come to dance, drink cheaply, and enjoy a late-night scene with real character. Cash-friendly and unpretentious.
A beloved Polish dive bar with a terrific jukebox, friendly staff, and cheap drinks that honor Division Street's Eastern European roots. Zakopane is small, unassuming, and utterly charming — the kind of place where strangers become friends over shots of Zubrowka. Old-school Chicago at its finest.