22 bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
Cleo's is the West Town sports bar that's always the right call — whether you're cheering on your favorite team, grabbing drinks with co-workers, recovering from a breakup, or just because you want a good pour. With a full food menu and a bocce court to keep things interesting, Cleo's brings laid-back neighborhood energy with enough personality to keep you coming back. It's the kind of spot where everyone feels welcome and the vibe is always on point.
The biggest Emporium location in Chicago packs the city's largest collection of classic arcade games, pool tables, and pinball alongside craft beer until 3am on Saturdays. Logan Square's ultimate low-key hang for competitive types.
An agave-forward cocktail bar on Milwaukee Ave that transitions from specialty coffee by day to mezcal and tequila cocktails by night, open until 2am. Logan Square's answer to wanting great drinks without the pretense.
Ukrainian Village's beloved dive bar has just enough updated charm to keep things interesting -- craft beer on tap, a loyal neighborhood following, and the kind of low-key energy that keeps the place buzzing until 2am.
Bucktown's neighborhood bar since 1988 hosts nightly live music spanning jazz, punk, and comedy in an intimate, art-filled room. It's scrappy, unpretentious, and still one of the best spots to catch a random great show on the North Side.
This West Town cocktail bar channels 1970s rock-and-blues energy with throwback vibes, creative drinks, and an atmosphere that feels like the golden age of vinyl. The Chicago Avenue strip location keeps it buzzing late into the night.
The West Loop's Grapes & Grains is a sophisticated piano bar and cocktail lounge with live music, networking events, and curated social experiences. The upscale atmosphere makes it a refined alternative to the neighborhood's louder options.
Division Street's Innjoy has been a Wicker Park staple for creative cocktails and a come-as-you-are atmosphere. The bartenders know what they're doing, the brunch draws a crowd, and the vibe stays consistently right.
Little Village's hidden speakeasy-style bar serves Latino-fused craft spirits and cocktails behind a discreet side-street entrance. The hearty entrees and craft beer round out a spot that rewards those who know where to look.
This sultry basement cocktail bar beneath Thalia Hall specializes in inventive punch bowls and craft cocktails in a retro-bohemian Pilsen setting. The subterranean vibe on 18th Street is moody, intimate, and built for a night that goes long.
Logan Square's definitive gin bar backs an inventive cocktail program with a lush backyard patio and a late-night menu that draws the neighborhood's creative crowd. The gin collection here is arguably the deepest in the city.
A spirit-forward cocktail bar housed in a converted 1920s Ukrainian Village social club, Sportsman's Club pours daily-changing drinks alongside an amaro machine and runs a curated bar-goods shop. The kind of place where the bartender is a genuine craftsperson.
Tucked inside Thalia Hall's restored carriage house, the Tack Room is an intimate Pilsen piano bar with live music Thursday through Saturday at 9pm. Craft cocktails in an old-world setting make it one of the most romantic rooms on 18th Street.
Locals know the Berkshire Room inside the ACME Hotel in River North (west) is where bartenders turn your taste buds into a cocktail menu—no two Dealer’s Choice drinks are alike. Open ’til 2am weekends, it’s the spot to sip precision-poured experiments in a lounge that feels like a secret.
Humboldt Park’s original speakeasy, The California Clipper has been pouring vintage cocktails and hosting live jazz since ’37—its mahogany booths and 3am Saturday curfew make it a time capsule for locals who know where to look. Seasonal drinks and a tavern soul that’s survived decades of Chicago nights keep the crowd loyal.
The Charleston’s weathered charm and ornate tin ceiling make it a Bucktown staple, where craft beers flow late into the night. Open until 2am weeknights and 3am Saturdays, it’s a no-frills hangout for locals who know the west side’s best-kept secrets.
Since 1992, The Empty Bottle has been Ukrainian Village’s gritty, music-obsessed heartbeat—dive-bar authenticity meets seven nights of indie rock, punk, jazz, and experimental acts, all with $3 PBRs until 2am. Skip the tourist traps; this is where the scene’s locals crowd the bar for cheap drinks and unfiltered energy.
Pilsen's go-to post-concert spot sits right across from Thalia Hall with affordable craft cocktails and a chill vibe that keeps the night going until 3am on Saturdays. It's the perfect second stop after a show on 18th Street.
Bucktown’s west side hides a travel-hungry tavern where beer geeks and early risers collide—The Map Room’s 1,500+ tap selection and 6:30am coffee runs keep it alive long after the last flight departs.
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.
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.
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.