Where to Eat Outdoors in Chicago, 2014 Edition


[Photograph: Nick Kindelsperger]

Coming off the most frigid winter most Chicagoans have ever experienced, we are extra hungry for some al fresco sunshine this year. So much so that we're willing to endure 40-degree May days and pretend like it's nice out in order to dine and drink on a patio—any patio. But when making those al fresco plans, make sure and park yourself at one of the city's best patios. Fortunately, the city is packed with some truly spectacular options, from tall rooftop bars to cozy neighborhood spots.

For Booze with a Stunning (and Safe) View: The dec Rooftop Lounge + Bar


[Photograph: Huge Galdones]

If you're like me, the problem with rooftop dining is vertigo, a problem not mitigated by the addition of booze. If there's one thing capable of dampening a nice view and a nice meal, it's the paralyzing fear of plummeting to my death. But of all the rooftop patios in all the land, the one that makes me feel most secure with my life is The dec Rooftop Lounge & Bar, situated snugly on the 12th floor of the Ritz-Carlton Chicago. With a gorgeous vista of Streeterville, and set back far enough to avoid a dizzying view down, this is the place to sip cocktails and nibble small plates. The menu changes seasonally, but make sure to share plates like crab-corn lollipops and bratwurst sliders, which are especially good when paired with cocktails like the Pomegranate Picnic made with pomegranate, blueberries, Cava, lemon juice, and Cointreau.

For the Backyard Party Feel, Minus the Annoying Relatives: Honey Butter Fried Chicken


[Photographs: Joe Roy]

There's just something about fried chicken that demands sunshine and warmth. So while you could just eat inside at Honey Butter Fried Chicken, everything seems to taste better sun-drenched patio. Bedecked with strung-up twinkling lights (who needs stars anyway?) and filled out with polished wooden tables, dining al fresco at this hip poultry parlor feels like a homey backyard shindig, albeit with far better catering then any backyard party has probably ever had. Naturally, you'd be remiss to come here and not order the fried chicken. These birds are sublimely crispy and juicy, especially when smeared in honey butter and paired with golden corn muffins.

For a Taste of Coastal Hipster Culture: Parson's Chicken & Fish


[Photograph: Joe Roy]

Proving that fried chicken and patios go together like beaches and sunscreen, another one of Chicago's preeminent outdoor settings can be found at Parson's Chicken & Fish. Unlike most restaurants and bars that tack on patios and rooftop bars as an addendum to their usual space, the patio at Parson's is its bread and butter. A vast majority of the seating at this boisterous Logan Square bastion is outdoors, nestled nicely alongside the open green space of Humboldt Boulevard. Row after row of picnic tables and umbrellas lend a coastal vibe to the space, accentuated by ping pong tables and a general aura of drunken glee. The chicken here is fried hard and dark, which is the way I like it. But even better are the hushpuppies, luscious little fritters of doughy cornmeal sheathed in a crispy exterior. The Negroni slushies live up to the hype, too.

For Pinky-Raising Elegance: Shanghai Terrace


[Photograph: Nick Kindelsperger]

For elegant dim sum tended to by graceful servers, head to Shanghai Terrace on the 4th floor of the The Peninsula Hotel. The outdoor terrace portion of this restaurant is open and spacious, with various kind of seating options, from traditional tables to lounge-y nooks akin to something you might collapse into while vacationing in Miami. The Magnificent Mile is located just outside, but thanks to the tall walls and lush greenery on the patio, the din is barely distinguishable. One of the best ways to take it all in is with the dim sum lunch, where small plates of refined dumplings, fluffy barbecue pork buns, and crispy wontons are whisked around the patio and into awaiting mouths.

For the Diner who Wants to Dine in a Garden: Homestead on the Roof


[Photograph: Roger Kamholz]

As the name suggests, rooftop dining is key at Homestead on the Roof. The seasonal restaurant comes to life during the warmer months, when the 80-seat patio opens onto a 1,000-square-foot organic rooftop garden. Though it's located on bustling Chicago Avenue, the vertical greenery and dozens of plant boxes brimming with produce and herbs, make it feel like you're dining in a secret garden. Taste the produce in new dishes like the kale salad with burnt cheddar and bacon-cider dressing; orecchiette strewn with pickled ramps and oxtail; and an excellent half chicken served with lamb sausage, golden raisins, fried artichokes, and roasted carrots.

For Parkside and Lakeside Views with a Side of Liquor: The J. Parker


[Photograph: Nick Kindelsperger]

Perched atop the Hotel Lincoln and directly across the street from Lincoln Park, The J. Parker offers views of Chicago's skyline and Lake Michigan that simply can't be beat. Thanks to clear panels surrounding the patio, you can take in the unobstructed views of the city. There's also a handy heating system to keep the space alive even when the weather decides to be awful.

Although this is mostly a destination for drinking, don't overlook the impressive bar food, which is tended by Paul Virant, a James Beard Award winner. The menu focuses primarily on shared plates and handheld items, like shrimp toast and a walleye pike burger. These will keep you going as you power through cocktails such as The Bearded Lady, made with rum, Creme de Violette, Prosecco, Earl Grey syrup, and lemon. And if you're looking for a more serious dinner, you always have Virant's more seasonally focused restaurant, Perennial Virant, on the ground floor.

For Cozy Neighborhood Serenity: Gather


Fried Chicken and Biscuits at Gather [Photograph: Chelsea Ross]

If you're looking for outdoor dining that is intimate and comfortable, no place nails it quite like Lincoln Square's Gather. This is a quintessential neighborhood restaurant, one where locals convene over plates of seasonal comfort food, like the chicken fried biscuit on the brunch menu, and "gathering boards" brimming with charcuterie and cheese. Located behind the restaurant, the enclosed terrace is a hushed retreat from the hustle of Lincoln Ave.

For Burgers and a Breath of Fresh Edgewater Air: Moody's Pub


[Courtesy of Moody's Pub]

One of the greatest al fresco surprises in the city can be found at Moody's Pub, an Edgewater institution that looks entirely nondescript and forgettable to the outside passerby. But make your way to the back, and you'll find yourself in one of the coolest patios in the city. The shaded, rustic courtyard is pretty rickety and no-frills, but in the same charming sort of way you'd feel about visiting your jovial aunt and uncle and hanging out on their back porch drinking beer. Make sure to pair that beer with one of the pub's signature Moodyburgers—a hefty slab of beef with an intense grilled aroma, on a sesame-crusted bun with minimal accoutrements.