Bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
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.
High-energy Wrigleyville bar with non-stop entertainment featuring live music and late-night DJs. A loud, always-buzzing spot near Wrigley Field.
Bartlett's TL's Four Seasons nails the fusion game—sushi-grade fish meets fire-kissed Szechuan, all under one roof. The kind of spot where families and foodies alike keep coming back, far from the city's glow.
Tong’s Tiki Hut in Villa Park is a neon-lit escape where bamboo shadows and lantern glow frame bold Chinese-Japanese bites—try the egg rolls with a mai tai, served under a roof that feels like a secret from the ’60s. Suburban nightlife just got an island twist.
High-tech driving range with climate-controlled hitting bays, full bar, and food menu. DJ and music on weekend nights. Groups up to 6 per bay.
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.
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.
Legendary 1950s-style retro diner. Tallow-fried burgers, hand-dipped milkshakes, and retro counter dining. Nostalgic, vintage, unpretentious. A Chicago South Side institution since the '50s.
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.
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.
Trickery offers an intimate, hilarious, and outrageous entertainment experience in Lakeview. The theater is BYOB for guests 21+, making it ideal for a unique date night or group outing. Talented performers blur the lines between illusion, mind-reading, and comedy — an unforgettable night out where reality is questioned and the impossible happens before your eyes.
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.
A Chinatown mainstay since 1994, Triple Crown still rolls carts loaded with classic dim sum down Wentworth Avenue. The Cantonese seafood banquets are the move for big groups looking to eat like royalty on the South Side.
Tuco and Flandie is a gourmet taco bar in Lincoln Park, serving Chicago's north side.
A Black, family-owned craft microbrewery in historic Bronzeville. Co-founders Steven Turner and Blair Turner-Aikens honor the neighborhood legacy with uniquely named beers including "The Helen" and "The Mabel." In a craft beer industry where Black ownership is less than 1% nationally, Turner Häus is one of the most important breweries in Chicago. The taproom is a community evening space loaded with card games, local art, and house-brewed pints.
Turtle’s Bar & Grill fuels Bridgeport’s south-side sports scene with wall-to-wall TVs and a wall of burgers, pizza, and post-game revelry spilling onto the sidewalk until 2am. One block from Guaranteed Rate Field, it’s where locals crowd the bar for games, beers, and the kind of rowdy energy that lingers long after the final buzzer.
Historic, intimate Old Town dive bar famous for its jukebox, heavy whiskey pours, and mobster-era history. Zesty BBQ ribs, buffalo wings, onion rings, and classic martinis. Operating since 1932.
Cozy cafe and lounge with artisanal pastries, locally sourced toast boards, and custom espresso. Intellectual, quiet, romantic. Stays open until 9PM for select evening acoustic date-night sets.
Naperville's go-to date-night spot sits above Potter's Place with dim lighting, elegant decor, and a martini menu that goes deep. Two-Nine sets itself apart from every other downtown Naperville bar with an intimate cocktail-lounge atmosphere built for conversation.