Bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
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.
Chicago's favorite sports bar since 1992, Timothy O'Toole's in Streeterville is the go-to destination for game days and nights out. With 72 HD flatscreen TVs, 48 beers on tap, award-winning wings, and a full menu including the legendary Big Timmy Burger (as seen on Man vs. Food), this multi-level bar is steps from the Mag Mile. Open late daily.
The 6th-floor Swing Suite at 900 N Michigan is where Streeterville's competitive set goes to settle scores over golf simulators and virtual sports—think zombie dodgeball between martinis. Full bar and elevated food menu keep things classy while you're crushing it at the virtual fairway. Best late-night option when you want gaming without leaving the architectural showcase that is North Michigan Avenue.
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.
Evan Funke's St. Regis showstopper in Downtown Chicago serves some of the city's most luxurious Italian—think silky handmade pastas and pristine bistecca Fiorentina under soaring 40-foot windows overlooking Lake Michigan. This is where serious money goes for serious food, with the kind of theatrical plating and wine program that makes a night here feel like an event. Book the Chef's Counter if you want to watch the pasta magic happen up close.
Tzuco is a michelin french-mexican fusion in River North, serving Chicago's downtown side.
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.
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.
Verilife in River North stays open till 10 PM, making it a late-night cannabis haven in the Mag Mile’s sleek downtown core. Known for smooth transactions and knowledgeable staff, it’s the go-to spot for discreet, high-end product picks after the bars close.
River North's Wake n Bakery serves up pastries and brunch in a cozy space that works as a low-key start to a bigger night out. Coffee by day, cocktails by evening, and a vibe that keeps things chill in one of the city's busiest neighborhoods.
Elevate your evening at the Willis Tower Skydeck, an iconic observation deck 103 floors above the Loop that offers breathtaking views and a premium night out.
Wintrust Arena in Chicago is a sleek, state-of-the-art venue renowned for hosting world-class concerts, sports events, and exclusive galas, offering an unique experience with cutting-edge technology and premium amenities. Its upscale atmosphere, combined with impeccable service and diverse entertainment options, makes it a top destination for discerning nightlife seekers in the city.
Intimate piano bar on State Parkway where sing-alongs and strong drinks have kept the Gold Coast entertained for decades. Zebra Lounge is a no-frills, vintage-vibes institution -- zebra print everywhere, a pianist who takes requests, and a crowd that actually sings along. Pure Chicago charm.