Patio season is prime time in Chicago, as the city officially emerges from its winter freeze and celebrates warmer weather in style. It’s the time of year when the city comes alive, and if there’s one thing locals are collectively good at, it’s making the most of patios and rooftops. Accordingly, al fresco restaurants and bars are widely available throughout the city, from see-and-be-seen downtown hot spots to tranquil neighborhood oases and hip haunts. Whether you’re looking for a cocktail-fueled photo op or a chill meal in Wicker Park, here is your ultimate guide to the 14 best patios and rooftops to hit up this summer in Chicago.
Devereaux: Soaring high atop the newly minted Viceroy Hotel Chicago, the Gold Coast’s hottest new terrace is sure to light up Instagram feeds this season. Technically, Devereaux emerged late last summer/early fall, but considering its al fresco opportunities were limited, 2018 feels like its fittingly grand debut. Complete with a sleek pool surrounded by chic lounge chairs and dazzling downtown views, the indoor-outdoor space provides quite the backdrop for some of the neighborhood’s most exciting cocktails. Like a daiquiri with kiwi and black lime, or a Campari-splashed rosé cobbler, or a Negroni infused with smoky tobacco bitters, mezcal and flamed citrus. Don’t sleep on the food menu, either, featuring shareable snacks and plates by acclaimed chef Lee Wolen, like oysters with yuzu kosho, roasted cauliflower hummus, beet tartare with cumin yogurt and fried chicken bites with sriracha aïoli.
RM Champagne Salon: Year after year, this clandestine Parisian-inspired parlor proves its longevity and solidifies itself as one of Chicago’s quintessential, timeless patio destinations. Nestled down a cobblestone alleyway off Green Street in the West Loop, RM is one of the most transportive, beautiful locales in the city. While the fireplace-clad lounge is a popular cozy hideaway in the colder months, the bar really comes alive in the summer, when Champagne-sippers can congregate on the gorgeous patio. Hidden away between buildings, away from the hustle and bustle, and lit up by twinkling bulb lights, it’s as pretty as it is romantic. Order up some oysters, some caviar, some sparkling rosé and call it a day well done.
City Mouse: Elsewhere in the West Loop, the Ace Hotel’s resident restaurant boasts one of the neighborhood’s most enormous patios. The sprawling al fresco space alongside City Mouse features two roaring fire pits for chillier nights, rows of bulb lighting and contemporary seating arrangements for larger groups or couples. Open all day long, the restaurant features brunch every day, happy hour and exemplary cocktails. It’s especially popular during the day, when guests can sip peach-banana smoothies in the sunlight, while noshing on frittatas, Brussels sprouts grain bowls and cornmeal griddle cakes with pork shoulder ragu and hollandaise.
Gibsons Italia: The ritziest new patio contender in town comes by way of the lauded Gibsons Group. Clocking in at three stories, the riverside Gibsons Italia piles on the decadence in every nook and cranny, and nowhere is this more evident than the restaurant’s rooftop terrace. Surrounded by glass and a retractable roof, the atrium-like space features a limited menu of shellfish, appetizers and panini, and a full bar, open to the public every Thursday, Friday and Saturday. Reservations are available for the couches and chairs, and walk-ins are accepted as well. Elsewhere in the restaurant, the dining room patio on level three contains seating for 68, while the bar patio on level two has a 32-seat deck of its own. No matter which floor you’re on, the views overlooking the Chicago River are unparalleled.
Noyane: Similar to other rooftop venues like Homestead on the Roof and Streeterville Social, Noyane is a seasonally exclusive restaurant that only operates late-spring through early-fall. That means you can only eat the coveted sushi when the weather is nice and the temperature cooperates. Located on the roof of the Conrad Chicago Hotel, the Japanese sensation serves pristine platters of nigiri, sashimi and maki, along with a vibrant menu of cocktails, Japanese whiskey, sake and wine. Completely exposed to the elements, save for a central bar with a small roof, the terrace is the perfect spot for soaking in the views and the Magnificent Mile vista. Snag a spot by the artsy fire pit if it cools off after sunset.
Apogee: Perched atop the Dana Hotel and Spa in River North, Apogee is a cocktail haven so whimsical and inventive that the drinks rival the views in terms of photogenic quality. Here, you’ll find cocktails in wonky hues and glassware, like a smoked floral libation poured out of a glass bong. There’s plenty of indoor space should the weather take a turn, but views can still be savored through floor-to-ceiling windows. Otherwise take your cocktails out onto Apogee’s outdoor deck, a space outfitted with modern furniture, faux grass, planters and a long central fire pit.
Cindy’s: You can’t talk about rooftops in Chicago without bowing down to the reigning queen. Few terraces are as popular (and perpetually packed) as Cindy’s atop the Chicago Athletic Association hotel. Lustrous inside and out, with immaculate cocktails and large-format dishes, Cindy’s is best known for its coveted views overlooking Millennium Park. The outdoor space gets crowded quick, so swing by in the afternoon to secure a spot. There are fire pits on either side of the deck, and a newly implemented outdoor bar to help mitigate the queue at the main bar inside. Aside from its views of the Bean, Cindy’s is best known for its exquisite cocktails. And for good reason. Try the endlessly popular Grey Garden, which has vodka, Dolin Blanc, creme de violette, Jasmine pearl tea and lemon, or the perfectly summery Howl at the Jun, which has sparkling rosé, grapefruit, kombucha and gin.
Piccolo Sogno: While the city is constantly adding hot new patio spots, there are still those venerable standbys that prove the test of time. Piccolo Sogno is one of those enduring gems. The River West Italian mainstay has one of the most beloved patios in town, filled with a veritable garden of planters and surrounded by tall fencing that serves to whisk diners away from the city noise and to a tranquil Italian hideaway. The vast patio is great for groups, and popular for business lunches, serving a crowd-pleasing menu of pizzas, pastas, antipasti and fresh fish dishes befitting lighter, more summery dining. To drink, skim the white wines selections from the restaurant’s enormous Italian wine list.
Chop Shop: Chop Shop’s clandestine, cozy rooftop deck may not be as visible or crowded as nearby spots like The Robey or Big Star, but that’s actually a benefit. The comfy space feels like a legit hidden gem, featuring umbrella-clad tables atop a chic wooden deck, providing the perfect platform for sipping your way through the restaurant’s brand new cocktail menu. Offering idyllic drink options for warm weather, selections include the Soggy Stardust, made with vodka, strawberry puree, Green Chartreuse, lemon juice and orange bitters; After the Snow, with pisco, green grapes, lemon juice, simple syrup and lime zest; ad Chupacabra’s Revenge, which combines mezcal and honey with grapefruit juice, lime juice, Cocchi Americano, amaro and seltzer.
Bang Bang Pie & Biscuits: Not all popular patios are about cocktails and dinner, as evidenced by the constant popularity of Bang Bang’s patio in Logan Square. When the sun is shining, locals clamor for picnic tables and lawn chairs in back of this adorable pie and biscuit shop. With a menu that rotates regularly, dessert options currently reflect summery cravings with slice selections like rhubarb pie, s’mores and key lime. Don’t miss the incredible, refreshing berry icebox pie, which tops shortbread crust and blueberry icebox cheesecake with a thin layer of raspberry gelee.
Parson’s Chicken & Fish: One of Logan Square’s most popular patios just got even better and bigger, with the brand new unveiling of Parson’s overhauled patio. The hip destination has become synonymous with summer over the years, beloved for its quenching Negroni slushies, fried chicken, picnic tables and ping pong table. Now that construction is over on renovations, the restaurant and bar boasts even more summery vibes. In addition to expanded indoor space, there are more tables and stadium-style seating outside, along with a funky new custom ping pong table and a bar lined with stools on two sides. To coincide, the kitchen has rolled out some new summer menu offerings to enjoy, like buffalo chicken wings, mac & cheese and chicken and waffles.
Big Star: It’s impossible to talk about patios in Chicago without mentioning the mighty Big Star. From the moment the hip taco haunt opens, every day of the week, the Wicker Park spot is mobbed with diners and drinkers. Endlessly popular and notoriously difficult to get into without having to wait on the sidewalk, the honky-tonk is revered for good reason. Along with a menu of quintessential patio fare (i.e. tacos, margaritas, beer) the enormous patio bustles with upbeat music and energy. Surrounded by planters, lit up with dangling bulb lights and shaded by yellow umbrellas, the space is pretty much perfect. For those looking for that Big Star patio experience without the wait, there’s an adjoining takeout window with ample picnic table-style seating of its own. The only difference, really, is there’s no booze sold from the window.
Small Cheval: What Big Star is to tacos, Small Cheval is to burgers. Bucktown’s hippest patio is a casual spin-off of the West Loop’s wildly popular Au Cheval, featuring a pared-down menu of all-American cheeseburgers and fries with drink options like beer, draft cocktails and milkshakes. Inside, seating is limited and the space feels dark and cavernous, which is certainly cozy and warming during the winter months. But when patio season strikes, lines start to wind out the door as locals seek sunny refuge with their comfort food. The patio is loaded with rows of spacious picnic tables, situated between the restaurant and a tall brick wall along the opposing building. There’s a fence sectioning off the patio from Milwaukee Avenue, making it feel like a sanctuary.
Mahalo: For true tropical vibes in Wicker Park, hit up this Hawaiian spot for piña coladas and poké on the roof. The interior spaces at this two-story restaurant and bar are vibrant and beachy enough as is, bedecked with surf boards and pastels, but the best seats in the house are on the second-floor roof deck. Out here, you’ll find rows of white tables and wooden banquettes resembling a beach-side motif, along with a couple circular tables and umbrellas. There’s a long row of surfboards along one wall, and twinkling bulb lights providing ambient glow.
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