New Wave Coffee
The chances of you picking up a bed-headed hottie while making your way through Logan are pretty good. The chances you’ll be able to, uh, entertain that hottie all night after several rounds of drinking? Not so great. That’s why you should start your night early (and sober) at this sidewalk patio, which boasts vegan sweets, $3 bottomless cups of Metropolis and late-night hours (till 11pm) to kick-start your debauchery. (Just pray the caffeine lasts you all night.) 2557 N Milwaukee Ave (773-489-0646).
Pity the beer drinkers who follow up their coffee with a pint at this gallery-cum-watering hole—they’re usually stuck in line behind people ordering Dark ’n’ Stormies and other complicated cocktails the bar’s known for. Warm weather solves the problem as the Whistler opens its back patio, a humble space rimmed with a few plants and outfitted with a beer bar, making the wait between you and your Three Floyds not only easier, but breezier. 2421 N Milwaukee Ave (773-227-3530).
90 Miles Cuban Cafe
You and that hottie are probably hungry by now, so seek out Alberto Gonzalez’s ropa vieja at his new location, where Gonzalez has blasted the former Calvin’s BBQ with colorful murals (seen here in progress) and set up umbrella-topped tables in the gated side patio. End your night with Cuban sandwiches and caramelized plantains while knocking back BYO Cuba libres under the stars—and maybe a café con leche, too, just to be sure. Slated to open late May. 2540 W Armitage Ave (773-342-5100).