It might not be a “four seasons” sort of outdoor dining city, but Chicago has plenty of al fresco options to offer. Whether you’re looking for an energizing cocktail after work or a delicious meal with friends and family, we’ve got you covered in the windy city.
Duck Duck Goat
Duck Duck Goat serves chef Stephanie Izard’s take on Chinese fare from dim sum style plates to noodles. It’s likely that you’ve never had many of the dishes on offer, and that’s the fun of this place. So dig in, try something new, and do it outdoors. The small, colorful patio seating might not give quite the atmospheric charm as the interior dining areas – but it may be easier to snag a seat, as it’s first come, first serve.
857 W Fulton Market, Chicago, IL 60607
Piccolo Sogno
Surrounded by various trees, vines, and bushes, Piccolo Sogno’s patio is a beautiful reprieve from the hustle and bustle of Milwaukee Avenue. The pizzas are hand-tossed, moderately priced, and baked in a wood-burning oven. The pastas are handmade and not overly delicate or rich, plus they make creamy gelato in-house..
464 N Halsted St, Chicago, IL 60642
Small Cheval
At the angular intersection of West Wabasania Avenue and North Milwaukee in Wicker Park sits Small Cheval, the marvelous little sister to Au Cheval in Fulton Market. The small menu features a handful of items crafted to perfection. Get the cheeseburger, add bacon and a side of golden fries, then top it all off with a beer or a chocolate shake. Enjoy it on the patio with friends, strangers, or no one – you’ll be so immersed in your food that lack there of, won’t even matter.
1732 N Milwaukee Ave, Chicago, IL 60647
Parson's Chicken & Fish
What screams summer more than eating fried chicken under a red and white striped umbrella at a communal picnic table with a negroni slushie? Nothing. And Parson’s provides it all. If frozen negronis aren’t your thing, no worries – get a beer on tap, house cocktail, or one of the other three frozen cocktails. If you prefer fish, and you don’t want it fried, order the ceviche. We love Parson’s Hot fried chicken, but if you’re feeding a group, go for the whole Fried Amish Chicken, and don’t miss out on the cheese curd fritters and hush puppies – a necessary compliment to your Parson’s picnic.
2952 W Armitage Ave, Chicago, IL 60647
Cindy's
If you have a large group of friends, family, or even strangers willing to share a meal, Cindy’s rooftop is one of the best places to grab dinner. The view over Millennium Park is unrivaled, the food comes family-style, the atmosphere is rambunctious, and the setting is sleek. Shrimp a la plancha, Mrs. R’s meatballs, and spring cavatelli are our top platter picks – but there’s hardly a way to do it wrong. As the sun goes down, the place gets even more beautiful, so time it right, and don’t forget to make a reservation.
12 S Michigan Ave, Chicago, IL 60603
Expat
This pop-up has tailored its menu and drink offerings specifically to compliment al-fresco dining. The light menu is refined, but still approachable, boasting oysters on the half shell, a selection of crudos, salads and sandwiches, and small plates like burrata with smoked trout roe, and raw vegetables with dip. Oh, and if you miss those freeze-pops from your youthful summer days on the playground, you’ll be happy to know that Expat is making them with gin, tequila, and rum.
118 N Green St, Chicago, IL 60607
Red Door
Named quite literally after the giant red door that opens into the restaurant, Red Door has an eclectic menu for both dinner and weekend brunch, as well as an outdoor patio complete with warm string lights zig-zagged overhead. Brunching outdoors is a fabulous way to spend a weekend morning, and we highly recommend doing it here. From duck chilaquiles to brioche French toast, steak and eggs to the smoked salmon bagel – it’s easy to find something that tempts you.
2118 N Damen Ave, Chicago, IL 60647
Bang Bang Pie Shop
For a casual, comfort food-filled meal, Bang Bang Pie is a favorite in Logan Square. Just the right amount of rustic and refined, get your pot pies, biscuits, grits, and slices of pie – then head out to the patio. Relax under the shade cast by umbrellas, while you ponder the ways of the world in between bites of tangy key lime or chocolate pecan pie. It’s the kind of space where you could sit for hours, and you just might.
2051 N California Ave, Chicago, IL 60647
