Bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
Offers breathtaking views of the Chicago skyline from the 96th floor.
The Signature Room, located on the 23rd floor of the Trump International Hotel in Chicago, offers panoramic views of the city skyline and the Chicago River, creating an iconic backdrop for upscale dining. Its sophisticated ambiance, paired with a curated menu and a lively bar scene, makes it a top for both fine dining and lively nightlife in the Loop.
A fun bar with a relaxed vibe, known for its cocktails and outdoor space.
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.
Laid-back Southern soul food lounge on the South Side featuring live jazz performances in an intimate setting. Known for down-home cooking and a warm, welcoming atmosphere.
A cocktail bar with a focus on seasonal ingredients and a rustic charm.
The Studebaker Theater, a historic Art Deco gem in Chicago’s The Loop, offers a unique blend of architectural elegance and lively nightlife with its eclectic lineup of concerts, comedy, and theatrical performances. Its intimate setting and iconic marquee make it a worth visiting destination for culture seekers and entertainment enthusiasts alike.
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.
lively, red-lit, intimate cocktail venue that packs out late at night. Features deep, soulful house music, live open mics, and experimental jazz sets that draw a highly creative, music-focused crowd.
Lakeview's legendary Vic Theatre has seen everyone from Bowie to Dylan to Coldplay grace its stage. Originally the Victoria Theater, it's an intimate spot that punches way above its weight for live music and comedy specials.
James Beard Award-winning cocktail bar hidden behind an unmarked facade. Seasonal craft cocktails, no-phone policy, and intimate candlelit atmosphere.
Lincoln Square's neighborhood gem serves bird-themed cocktails and inventive New American plates with a charming patio. The rotating seasonal menu rewards regulars who keep coming back to see what's new.
Offers an extensive whiskey selection and a relaxed vibe.
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.
Catch post-show crowds and wall-to-wall game coverage at this modern sports bar near the amphitheatre, where the kitchen stays open until 1am for late-night bites. It's the reliable spot to debrief after a concert without pretension or overpriced cocktails. The vibe skews loud and celebratory—perfect if you want energy over ambiance.
Wicker Park's legendary late-night spot serves Chicago-style hot dogs and Italian beef until 4 a.m., making it the ultimate post-club refuel for anyone worth knowing. The counter staff's notoriously sharp banter is part of the charm—don't take the sass personally. This place has been slinging iconic Chicago eats since 1983, and it's where the night actually *ends* for serious partiers.
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.
River North's Three Cities Social Club is a stylish venue hosting professional networking events, summits, and upscale social gatherings. The crowd skews ambitious and well-dressed — bring business cards.
Three Dots and a Dash in Chicago is a sleek, speakeasy-style venue known for its inventive cocktail menu and engaging, retro-inspired ambiance. Its intimate setting and curated live music nights make it a standout spot for those seeking a sophisticated yet lively nightlife experience.
This charmingly nostalgic eatery is deeply loved for its traditional Cantonese dishes and classic dim sum steam carts. Regulars love the generous portion sizes and flavorful executions of comfort foods like Mongolian beef and roasted duck. The quiet, relaxed environment offers a wonderful escape on a late weekend night — a timeless, highly reliable Chinatown staple.
Jeff Award-winning TimeLine Theatre brings history to life through powerful plays in their new Uptown home at Broadway and Argyle. The company specializes in time-bending productions that connect the past to right now.