Bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
Concert venue in Wrigleyville at 4039B North Ravenswood Avenue.
Bandit is a sleek Chicago cocktail bar hosting happy hours, networking events, and social gatherings.
Wine and cheese parlor in Lakeview with a small-plates menu. Curated wine list, artisanal cheese selections, and a quiet, intimate setting for a relaxed evening.
Comedy club in Lakeview at 2831 North Broadway.
This Roman-inspired wine bar on Andersonville's Clark Street strip pairs house-made pasta and wood-fired dishes with Italian-focused craft cocktails. The daily happy hour pulls in the neighborhood crowd, and the candlelit dining room is a proper date-night spot.
BaseCamp Pub keeps it raw in Lakeview with underground DJ nights, punk shows, and the kind of divey energy that bigger venues can't replicate. Cheap drinks, loud music, no pretense.
River North's most seductive steakhouse wraps bone-in ribeyes, live jazz, and dim speakeasy glamour into one of the hardest reservations in the city. The old-school cocktails hit as hard as the bill, and every detail — from the red leather booths to the tableside presentation — says this is a proper grown-up night out.
A small-batch craft brewery on Malt Row with a dog-friendly taproom, board games, skee-ball, and rotating food trucks -- Begyle is North Center's most chill neighborhood hangout in the Ravenswood Industrial Corridor.
Big Jones in Andersonville serves refined Lowcountry and Cajun cuisine sourced from 40+ local farms, delivering authentic Southern comfort with serious culinary chops. This farm-to-table gem is where Chicago's food-obsessed locals go for heritage recipes executed at a level that respects both tradition and technique.
An indoor mini golf bar in Lakeview with arcade games, craft cocktails, and a playful atmosphere. Artist-designed holes and a laid-back vibe make it perfect for date night.
Billy Sunday is a vintage amaro cocktail bar in Logan Square, serving Chicago's north side.
Tucked into Lincoln Square with a beautiful garden patio and classic Provencal dishes, Bistro Campagne is one of the best date-night restaurants on the North Side. The wine list is deep, the atmosphere is charming, and the French cooking is the real deal.
Venue in Lakeview at 3357 North Lincoln Avenue.
An acclaimed professional theater company dedicated to producing plays, musicals, and performances celebrating African American culture and history. Founded by Jackie Taylor, it presents world-class productions featuring blues, jazz, and theatrical performances on Chicago\x27s North Side.
Blazed Bakery Chicago is a cannabis-infused cafe in Logan Square, serving Chicago's north side.
Speakeasy bar in Lakeview at The Den Hotel. Also listed as Room 13.
Boka's Lincoln Park location serves as the gold standard for Chicago date nights, with Chef Lee Wolen's seasonal American tasting menus delivered in an intimate, garden-enclosed dining room that feels like a secret. This Michelin-starred kitchen doesn't play it safe—expect precise technique and unexpected flavor combinations that justify the price tag and the reservation battle.
Venue in Andersonville at 4901 N Clark St..
Behind a hidden grass door on Division Street in Wicker Park lies Bordel, a Parisian-inspired speakeasy lit entirely by candlelight. Nightly jazz, burlesque, and live entertainment share the room with savory small plates — it's moody, romantic, and very hard to leave.
This energetic spot on Clark Street doubles as a lively neighborhood community lounge serving classic Cameroonian and Central African street food staples, including seasoned grilled brochettes and roasted fish. Open late into the night with weekend music mixes, soccer match watch parties, and smooth lounge vibes — a fantastic social hotspot to share a drink and enjoy deep, savory finger foods into the early morning.
Andersonville newest gem for arts and culture. The Bramble Arts Loft occupies the second floor of the historic Capital Garage building on Clark Street, featuring The Beatrice (101-seat thrust theater), The Berry (900+ sq ft black box), and The Cabaret, a cozy intimate performance space. Home to Bramble Theatre Company, a 501(c)(3) nonprofit — 100% of venue profits support equitable arts access across Chicago.
Nightclub in Lincoln Park at 2265 North Lincoln Avenue.
A destination for lively drinks and convivial dining on the third floor of the legendary Waldorf Astoria Chicago. Brass Tack serves French-American cuisine with a modern twist — shareable plates, craft cocktails, and an expertly curated wine list — in a laid-back yet upscale Gold Coast setting. With a renowned bar area, private dining options, and stunning Gold Coast views, it is the quintessential Chicago date night spot.
A top mid-size Broadway venue in the heart of the Magnificent Mile, housed in the northeast corner of Water Tower Place. Originally built in the 1970s as The Drury Lane Theatre, the Broadway Playhouse at Water Tower Place is part of the Broadway In Chicago family and hosts touring productions in an intimate 590-seat setting — just steps from Michigan Avenue.