Bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
Certified VPN Neapolitan pizzeria in Ravenswood with a wood-fired oven imported from Italy and pies that rival anything in Naples. The gorgeous patio is a neighborhood treasure -- walk-ins welcome, reservations by phone.
Spybar, located in Chicago's lively River North district, offers an exclusive blend of sophisticated ambiance, cutting-edge mixology, and engaging entertainment that defines the city's elite nightlife scene. Its iconic rooftop terrace and curated events make it a worth visiting destination for discerning patrons seeking unparalleled luxury and innovation.
Features a rooftop bar with stunning views of the city skyline.
Historically inspired cocktails, quirky decor, and a dog-friendly all-season patio anchor this River West cocktail spot in West Town. Late-night hours until 3am on Saturdays and a personality that sets it apart from the cookie-cutter bar scene.
The Playpen is Chicago's legendary lakefront marina and gathering spot on Lake Michigan, just north of Navy Pier. Every summer it becomes the backdrop for the Chicago Scene Boat Party and other large-scale water events, where dozens of boats raft together for floating celebrations. The adjacent Ohio Street Beach makes it a top warm-weather destination.
Hyde Parks top live music venue and restaurant. Multi-level space with a concert hall, full restaurant, and rooftop. Features jazz, R&B, soul, and DJ nights with craft cocktails.
Offers breathtaking views of the Chicago skyline from the 96th floor.
A fun bar with a relaxed vibe, known for its cocktails and outdoor space.
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.
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.
Head northwest to Schaumburg and you'll find a three-story playground that blends golf with serious nightlife—100-plus climate-controlled bays, craft cocktails, and a rooftop that keeps the party going until 1am with fire pits doing heavy lifting on those crisp Midwest nights. It's not your traditional Chicago scene, but for the North Shore crowd craving competition without leaving the suburbs, the tech-enabled bays and full bar make it a legit 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.
Logan Square's Utopian Tailgate combines a spacious rooftop with big-screen sports and a lively bar atmosphere. Day parties and seasonal events make it a neighborhood favorite for those who want their sports-watching with fresh air and good drinks.
Roscoe Village's candlelit wine bar pairs an outstanding list with artisan cheeses and seasonal small plates. The patio has quietly become one of the most romantic spots on the North Side -- a perfect date-night play.
Rooftop lounge in the South Loop with panoramic city views. Hosts Afrobeats day parties, bottle service, and upscale events. Trendy, elite, sophisticated.
Downtown Tinley Park's outdoor event plaza. Weekly summer concert series with classic rock bands every Saturday night. Festive, open-air, welcoming.