Bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
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.
Black-owned wine bar in Bronzeville. Curated wines, charcuterie boards, and live jazz nights. Perfect for a sophisticated date night on the South Side.
Fulton Market's City Winery pulls off the rare trick of being a legit working winery and top-tier live venue rolled into one—catch indie acts and comedians while actual wine ferments behind the scenes. The vibe hits different when you're sipping something they literally made in the basement while a band tears it up on stage. Weekends go till midnight, so there's real breathing room to hit this before or after your next spot.
Lakeview's most swoony spot for date night, where French-Italian small plates and a seriously curated wine list pair perfectly with the kind of fireplace glow that makes you lose track of time. Food & Wine named it the most romantic restaurant in Illinois for good reason—the intimate lounge setup practically demands you linger over another glass. Come hungry for sophistication but plan to stay for the vibe.
Humboldt Park's essential natural wine and craft beer bar pairs a standout bottle list with seasonal small plates that are just as compelling. It's the neighborhood's best date-night anchor, tucked into a cozy room on California Avenue.
SixtyFour Wine Bar & Kitchen is Naperville's go-to for serious wine lovers—their rotating list of 64 by-the-glass selections pairs perfectly with chef-driven seasonal small plates that actually justify the splurge. Catch live music on summer Fridays and you've got the kind of date night that feels effortless but feels premium.
Evergreen Park's cozy wine bar on 95th Street offers curated wines by the glass, craft beers, and small plates in a warm, welcoming setting. Spoke & Vine is the south suburb's quiet answer to the date-night question.
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.
Since 1994, Webster's has been Logan Square's go-to for natural and minimal-intervention wines in a space that practically demands you linger past last call. The intimate vibe makes it the rare Chicago wine bar that works equally well for serious collectors and first-date nerves. Open till midnight on weekends, this is where the neighborhood's wine crowd actually hangs.