Epic Sky No one at Epic restaurant’s rooftop lounge seems to be worrying much about the drinks (boozy cocktails), the food (small plates like potato gnocchi with lamb sausage from the restaurant below) or the view (a third-story close-up of nearby buildings). The point is you’re a few stories up, at a stark white bar or on a sleek white couch, and even the fact that you’re holding a plastic cup can’t stop you from feeling glamorous. 112 W Hubbard St (312-222-4940). Sun–Wed 4pm-midnight; Thu 4pm-1am; Fri 4pm-2am; Sat 4pm–3am. Rooftop closes nightly at midnight. Average cocktail: $12.
Frontier So the hipster-vintage-saloon aesthetic-of-the-moment and a taxidermy grizzly bear wander into a sports bar. That’s pretty much the setup of Frontier, a tavern from the folks behind Lottie’s and the Pony, which mashes North Woods lodge elements into the neighborhood-tap mold. Chef Brian Jupiter’s food—char-broiled oysters, sliders and even whole-animal feasts—adds another wild card to the mix, and the more time you spend eating impressive dishes like the pan-roasted wild striped bass in the enormous side garden, the faster it all starts to come together. 1072 N Milwaukee Ave (773-772-4322). Brunch (Sat, Sun), lunch, dinner. Average main course: $15.
Kuma’s Corner The servers here sport more ink than a Bic factory, and the metal is cranked up so loud you can’t hear yourself talking, but therein lies the charm of the tucked-away side outdoor patio. What’s the draw? Well, the Slayer burger, for one—a pile of fries topped with a half-pound burger, chili, cherry peppers, andouille, onions and Jack cheese on a pretzel bun. That, and the extensive menu of craft beers, including plenty of limited-edition local brews to get before they’re gone. 2900 W Belmont Ave (773-604-8769). Lunch, dinner. Average main course: $12.
Longman & EagleThere will be strategically scruffed dudes, waifish women in grandma sweaters, flannel as far as the eye can see. This place is owned in part by the Empty Bottle guys, after all. But these are hipsters who know hospitality and a chef (Jared Wentworth) who knows pub grub: His menu changes often, but we’ve seen him turn the quizzical texture of beef tongue into a hash alternately crisp and fatty, and deep-fry clams to perfection. If eating in a dimly lit bar isn’t your summer fantasy, snag a seat on the patio on the tree-lined residential street. 2657 N Kedzie Ave (773-276-7110). Brunch, lunch, dinner. Average main course: $18.
Maude’s Liquor Bar Start by gulping down delicious whiskey smashes and stabbing at shellfish towers (on the small front sidewalk patio if it’s sunny). Then nosh on butter-smooth chicken liver mousse slathered on toast with shallot marmalade; nibble on smoky slabs of pork belly, fanned over a pitch-perfect salad Lyonnaise; and tear into roasted farm chicken. The embarrassment of riches will come to a halt at dessert as only three options (crème brûlée, chocolate mousse and maître d’ platter) are available. It’s a display of brass that would be maddening—if only the crème brûlée weren’t so dead-on. 840 W Randolph St (312-243-9712). Dinner. Average small plate: $12.
Old Town Social The yuppie crowd at this glamorous bar might have other things on its mind, but to come here and not order chef Jared Van Camp’s charcuterie is to miss the point: More than a dozen varieties are cured in-house, including standouts like the fennel-scented finocchiona. And the kitchen doesn’t stop there: Everything from the hot sauce to the hot dogs is made from scratch. Escape the TVs with a seat on the 60-seat sidewalk patio. 455 W North Ave (312-266-2277). Mon–Fri 5pm–2am; Sat 11am–3am; Sun 11am–2am. Average main course: $11.
Rootstock Wine & Beer Bar The novella-length menu at this low-key alcove contains loving and helpful descriptions of an impressive selection of wines and beers. And thanks to the full menu being available until 1am, this is the kind of warm, simple neighborhood place you’ll never want to leave—particularly if you can score a spot at one of the communal outdoor tables. 954 N California Ave (773-292-1616). Mon–Sat 5pm–2am; Sun 11am–4pm. Average main course: $11.