When you’re expecting mail from Hogwarts: Plymouth Grill | (Loop | 327 South Plymouth Court) The breezy rooftop deck sits just above an El platform and just under the wise, watchful gaze of one of the Harold Washington Library’s giant owl gargoyles. Homestead on the Roof | (Ukrainian Village | 1924 West Chicago Avenue) This restaurant is only open seasonally and accessible through a semi-secret entrance in Roots Handmade Pizza—good for times when you want to feel like a tween pop star. When you’re feeling European: Gene’s Sausage Shop | (Lincoln Square | 4750 North Lincoln Avenue) Speckled with flowers, tomato plants, and potted herbs, the rooftop beer and wine garden hosts a European style of outdoor dining. Summer smells drift through the wooden tables as patrons enjoy preservative-free grilled sausages that are ground and seasoned in house. Medici on 57th | (Hyde Park | 1327 East 57th Street) This University of Chicago campus institution houses a deli, a bakery, and a restaurant all under one roof—but where the roof ends is where the summer fun begins. Sip a fudge-banana-nut milkshake out on the elevated patio, or BYO favorite bottle of wine to pair with a mediterranean pizza scattered with goat cheese, black olives, sun-dried tomatoes, and pesto. When you can’t get a Will Smith music video out of your head: Roof on theWit | (Loop | 201 North State Street) Bienvenidos a Miami: the all-white decor, the neon lights, the dancers shaking it to the DJ’s beats—if it weren’t for the surrounding skyscrapers, you could fool yourself into hearing the ocean in the distance. Epic Sky | (River North | 112 West Hubbard Street) Visitors seated at low-slung tables can pass small plates, such as rabbit-sausage pot pie or lobster agnolotti, from the highly praised menu of the restaurant below, or lounge at cabanas while sipping drinks from the sleek, backlit bar. Zed 451 | (River North | 739 North Clark Street) Guests fill up on Brazilian steaks and other grilled meats on the all-wood roof deck framed by real grass grown to fit perfectly between toes. When you want to talk to seagulls, the angry loners of the avian world: Castaways | (North Avenue Beach | 1603 North Lake Shore Drive) Watch the volleyballers volley and the beach bums bum as you snack on sandwiches and salads and sip tropical libations. J. Parker | (Lincoln Park | 1816 North Clark Street) Award-winning chef Paul Virant crafts a small but thoughtful menu for diners as they enjoy unobstructed views of the park and lake. When you want to be deliciously overwhelmed with choices: Fountainhead | (Lincoln Square | 1970 West Montrose Avenue) Here, artisanal plates are designed to be paired with selections from the vast beer and spirits list rather than the other way around. Pegasus Restaurant and Taverna | (Greektown | 130 South Halsted Street) The full menu is not available on the veranda, but a huge list of more than three dozen small plates is. Pass around portions of seasoned lamb riblets, potato and sausage croquettes, and braised baby eggplant to feel like you’re enjoying an evening in Athens. When you want to imagine smashing a guitar: Reggies | (South Loop | 2105 South State Street) By night, rock bands take the stage; during the day, gamers soak in the sun while tossing bean bags or playing pop-a-shot. Bottom Lounge | (West Loop | 1375 West Lake Street) Under the Lake Street El tracks, this music venue serves up pints of Éphémère alongside beer-steamed mussels with bacon and leeks—one of the many pairing suggestions on the menu.