Bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
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 local favorite: 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.
Legendary Chicago nightclub that has been a cornerstone of the city's electronic music scene for over a decade. The MID features a state-of-the-art sound system in a warehouse-style space that fills with house, tech house, and EDM fans every weekend. Top touring and local DJs rotate through the booth regularly.
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.
First and only upscale dine-in restaurant in North Lawndale. Elegant atmosphere for date nights. Founded by Chicago native Chef Quentin Love. Closed Mon-Tue.
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.
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.
engaging, joyful live Caribbean music venue. High-energy reggae bands soundtrack a room packed with people enjoying jerk chicken and cold island beers. Chicago's top reggae destination.
Chicago's top private boat cruise and architecture tour operator, departing from their dock at 900 S Wells St. With 15,000+ five-star reviews, Tours & Boats hosts everything from intimate architecture tours to large-scale private cruise events on the Chicago River and Lake Michigan. The dock location features convenient parking right on-site.
A Black-owned Caribbean-fusion supper club in the West Loop — now rebranded as In Session: Soundbite Lounge, putting live DJs and performances front and center alongside truffle mac, smash burgers, and craft cocktails in a sleek dinner-party atmosphere.
Chef Stephen Sandoval's West Loop steakhouse blends Latin heat with prime cuts, pairing globally sourced beef with show-stopping ceviche. Late-night weekend energy and a Fulton Market address make Trino a destination for those who want more than a standard chophouse.
Dark old-world tavern down a cobblestone alley in Fulton Market. Plush leather booths, heavy pours, and an atmosphere that feels like a private club from another century.
A floral-forward Latin brunch and dinner spot in West Town — cochinita pibil tostadas, churro French toast, and craft cocktails in a lively, intimate room designed for long Saturday meals.
West Side legend since 1963 — and the birthplace of mild sauce. Gus W. Rickette Sr. and Mary F. Rickette started this as G & G Chicken Shack before renaming it Uncle Remus in 1969. In the late '60s, Gus noticed customers mixing ketchup and hot sauce on their chicken, so he created a proprietary blend that became THE mild sauce — now replicated at chicken shops across Chicago. Black-owned and women-led (now run by daughter Charmaine Rickette Alfred), Uncle Remus is where Chicago's fried chicken culture was born. The saucy fried chicken is cooked crispy and slathered in that original mild sauce. Also has a food truck and catering.
Pitchfork Music Festival takes over Union Park every July with cutting-edge indie, hip-hop, and electronic acts curated for people who actually care about music. Three days of discovery in one of the West Side's best green spaces.
The Near West Side's 23,500-seat powerhouse is where the Bulls and Blackhawks bring the electricity — and when there's no game, the concert lineup doesn't let up. If it's a big-name act or a sold-out playoff, this is where Chicago shows up.
Theater in Humboldt Park at 2620 W. Division St.
Swanky, sophisticated waterfront lounge with low lighting, luxurious finishes, and a high-end adult crowd. Ribeye Tacos, Crab Tostadas, Premium Mezcalitas, High-end Tequila Selections.
Bar in Little Italy at 1449 W. Taylor St.
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.
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.
West Side institution for gyro cheeseburgers, the classic Chicago VL burger. Fast food done the Chicago way — gyro meat on everything, open late, no frills.