Chicago’s 10 best outdoor dining setups

Skewing more modern than traditional, this River North steakhouse has long been a magnet for those who can’t get enough of dry-aged steaks and a sophisticated wine list. Chicago Cut counts President Obama as a fan. While the floor-to-ceiling windows give those dining inside a great view of the nearby Chicago River, the restaurant’s spacious outdoor patio offers an unobscured front-row seat to the boats passing by and the iconic skyscrapers across the river. Come before sunset to take full advantage of the stellar view.

Pilsen Yards is known for live music, vinyl DJ sets, and a secret speakeasy-style bar in the back. But you’re most likely here for the massive patio. It’s partially covered with exposed wood beams and overhead heaters (should cooler temperatures prevail). It features its own bar plus a fire pit, making it well-suited for a plate of fish or slow-roasted pork shoulder tacos (served on handmade tortillas) and a pitcher of margaritas or on-draft sangria.

The Dawson’s River West patio—a popular outdoor perch—is one to behold. Glass, brick, wood, and ivy come together to create a dazzling effect. The chic atmosphere is both relaxing and energizing, accompanied by solid American fare such as sticky duck wings, chicken-fried lobster, and charred cauliflower with agave vinaigrette.

It’s hard to know where to look first when sitting outside on the riverfront patio of this River North restaurant. Look south and you’ll see the Chicago River and its steady parade of boats. To the left and right are two of the city’s beautiful bascule bridges. And behind you is the pretty brick façade of the historic landmarked building that River Roast calls home. The dishes are equally artful, ranging from charcuterie boards and colorful salads to its namesake shareable roasts, including lamb, chicken, and whole fish. Come hungry and ready to snap plenty of selfies.

MICHELIN-starred Boka, a James Beard Award winner, delights diners with playful yet refined dishes such as brown butter roasted Atlantic cod with celtuce, beech mushrooms, and kombu (kelp) from chef Lee Wolen. While the skylight patio and preserved moss wall satisfy the need to be outside during Chicago’s colder months, the Lincoln Park restaurant offers two outdoor spaces once the weather warms up. Head to the tree-lined back patio for a cozy vibe or take in top-notch people watching at one of the three tables along the plant-filled entryway path—the latter is ideal for a pre-Steppenwolf dinner.

You might know chef Stephanie Izard from her time on Top Chef. You might know her for her flagship restaurant Girl & the Goat. If you want a taste of Izard’s award-winning cuisine al fresco, head to Cabra. This Peruvian-inspired restaurant on top of the Hoxton hotel in the West Loop is one of the few spots in Chicago where you can indulge on ceviche and pisco sours poolside while taking in the stellar city views.

Experience star chef Art Smith’s American farm-to-table fare on the Blue Door’s plant-filled patio, complete with chandeliers to match its tony Gold Coast surroundings. Smith’s famous buttermilk fried chicken is a must-order, along with signature dishes such as shrimp and grits, deviled eggs, salmon en croute, and key lime pie, which is topped with whipped cream, macadamia praline, and burnt honey caramel.

Kitsch reigns at Paradise Park’s trailer park-themed outdoor patio. Striking design details in the large covered yard include a RV, flamingo ornaments, swing sets, neon signage, and brightly colored mismatched chairs. On the food front, there’s a whole lot of pizza, plus nachos and salads. Cocktails with names such as Hot Girl Summer (Watermelon Red Bull, vodka, aperol, and lemon) and Hangover Iced Coffee match Paradise Park’s tireless party vibes.

Romance is alive and well at Piccolo Sogno, which means “little dream” in Italian. A large ivy-covered tree anchors the Italian restaurant’s tented backyard, where twinkly lights and foliage contribute to a scenic ambiance. The seasonal menu from celebrated chef Tony Priolo focuses on rustic Italian dishes such as black spaghetti with mussels, clams, shrimp, and calamari; braised beef short ribs over local white corn polenta, and ​​prosciutto di Parma pizza. An all-Italian wine list complements the hearty food.

The last thing you want while enjoying Chicago’s short but sweet summer is to waste time fighting for a patio table. Opt for one of the West Loop’s larger outdoor expanses at Recess to avoid that struggle. This sprawling patio has plenty of seating options, from high-tops on the turf to seats inside repurposed shipping containers. Take your pick and enjoy an assortment of burgers and hearty sandwiches alongside refreshing cocktails, such as the Monkey Bars with whiskey, blackberry sage shrub, and Demerara syrup. Groups can opt for larger cocktails such as the Teacher’s Pet (gin, aperol, lemon, and sparkling wine) while brunch-goers have the option of boozy cereal bowls.