Scofflaw
This place delivers the perfect ambiance: It’s intimate (but not over the top), quiet (but not pin-drop silent), and equipped with the all-important fireplace. Arrive before 7 p.m. to nab a spot in the smaller, less bustling back room, where the clustered chairs and couches let you cozy up while you chat. The tunes are vintage, and the cocktails—a nice mix of gin-forward classics and sweeter novelties, all under $10—may be even better than your company. Coyly brush hands over an order of skinny fries to seal the romantic deal. Logan Square, 3201 W. Armitage Ave., scofflawchicago.com
Ada Street
Candlelit and tucked away in a dark corridor near the river, this place is romantic without fuss or formality (evidence: records on the shelves and a Ping-Pong table on the patio). Come for dinner, or take a seat at the bar for wine or a bourbon-focused cocktail such as Second Hand News, a hot drink with cider, allspice dram, and mint that’s guaranteed to get you both feeling warm and fuzzy. Noble Square, 1664 N. Ada St., adastreetchicago.com
Fountainhead
This is the spot to impress a nearly significant other with your alcohol knowledge. The drink list is as long as the lingering stares you’ve been sharing: a rotating selection of 28 beers on tap and tons of reasonably priced whiskeys, which means you can order a few of your favorites for an impromptu taste test. Split a couple pours of Scotch and some appetizers, then share a cab home. Ravenswood, 1970 W. Montrose Ave., fountainheadchicago.com