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Chicago’s Best Patio Dining: A Quick and Easy Guide

When consumed al fresco, anything tastes better. Combine that fact with Chicago’s food scene, what I believe to be the best culinary climate in the world, and you have a summertime full of outdoor dining on too narrow sidewalks under wobbly and dusty umbrellas. Of course, as far as patio dining goes, there are the outliers. Some restaurants take their décor and presentation as seriously out-of-doors as they do inside. Their courtyards are well manicured, their slushy machine is dripping frozé, and their outdoor firepits are ready for those unseasonably cool nights.

Competition is high, but these are the clear stand-out winners for Chicago’s best patios in 2018.

(Looking to take the party from the sidewalk to the roof? Check out our guide to Chicago’s Best Rooftops!)

Chicago’s Best Outdoor Dining

Best Frozen Cocktails: Parson’s Chicken and Fish

Best Fish Tacos: Big Star

Best Prohibition Era Cocktails: Sportsman’s Club

Best Overall Scene: The Dawson

Best for a Date Night: Piccolo Sogno

Best for a Lunch Hour: South Stanley McCormick Memorial Court (Art Institute of Chicago)

Best Patios in Chicago: ParsonsBest Frozen Cocktails: Parson’s Chicken and Fish

2952 W Armitage Ave, Chicago, IL 60647

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Bring your posse and bring your dog. Be ready to sip the best Negroni slushies (and probably the only Negroni slushies) you’ve ever had. Play a few rounds of Jenga before devouring a ginormous Amish chicken sandwich, all for less than the cost of an hour parking downtown. These and other wonders await you at Parson’s newly remodeled (and expanded) patio. It’s going to be a chicken fried summer, ya’ll!

Recommendations

Eat: Hot Chicken Sandwich with House Made Potato Chips ($11!!!)

Drink: The Original Negroni Slushy

Best Patios in Chicago: Big StarBest Fish Tacos: Big Star

1531 N Damen Ave, Chicago, IL 60622

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If you’re still into Violet Hour (and you really should be!) across the street, start the evening at the prohibition-era lounge’s cousin Big Star. Eat enough fish tacos (some of the best in the city) to hold you over during the hour wait in one of VH’s queue.

Recommendations

Eat: Taco de Pescado

Eat: Taco al Pastor

Drink: House Barrel Whiskey

Best Patios in Chicago SportsmanBest Prohibition Era Cocktails: Sportsman’s Club

948 N. Western Ave, Chicago, IL 60622

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I don’t know why exactly so many love this patio, but we do — I’m including myself in that group. Especially in the winter, with the outdoor fireplace roaring, this bar and backyard feel to me like a relic from a truer time. Polished wood, hanging antlers, and a classic bar with an old-timey register ensure this spirt-forward establishment stands out as something for those serious about their booze. The patio is simple, almost domestic. The cocktails here aren’t gimmicky. They’re genuine, honest. Nothing’s plastic at Sportsman. Speaking of which, cash only.

Recommendations

Drink: Something of which your grandfather would approve.

Best Chicago Patios the dawsonBest Overall Scene: The Dawson

730 W Grand Ave, Chicago, IL 60654

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The gathering place of Chicago’s River West neighborhood boasts another outdoor fireplace that’s one of my favorites. I’m not sure when River West became the West Loop’s understudy in award-winning cuisine, but there are a few restaurants in these blocks that have built years of reputation on unforgettable, imaginative plates. The Dawson is one of these spots. In addition to items like their well-known Chicken-Fried Lobster and House-Made Cavatelli, their cocktail service aims to wow, and often succeeds. The crowd here tends to be laid-back and unpretentious, and their patio’s the perfect spots for a date or group of friends in the evening, under the stringed lights.

Recommendations

Eat: Chicken Fried Lobster

Drink: The Cool Kids Cabin (Bourbon and St. Germain? Yes, please.)

Best Patios in Chicago piccolo sognoBest for a Date Night: Piccolo Sogno

464 N Halsted St, Chicago, IL 60642

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If you can’t make it to Florence for dinner, head to Piccolo Sogno, another gem of River West. Opening this restaurant, was a “little dream” of chef Tony Priolo who got his start at age eight working in the cozy kitchen of his Sicilian grandmother. Dishes are prepared by hand with fresh, seasonal ingredients. Enjoy the Spaghetti Neri and a glass of vino from their extensive all-Italian wine list, on an isolated patio that feels Skymiles away from the city.

Recommendations

Eat: Spaghetti Neri

Drink: Pinot Noir

Best Patios in Chicago art instituteBest for a Lunch Hour: South Stanley McCormick Memorial Court

111 S Michigan Ave, Chicago, IL 60603

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No, this isn’t a restaurant, and there aren’t exactly any tables or chairs. Still, sitting at one of the fountains in the Art Institute’s beautiful garden respite is one of the best ways to spend any lunch hour. Emerge rejuvenated from the relaxing courtyard thanks to the beautiful trees that line its paths and the splish-splash of its water display.

Recommendations

Eat and Drink: Something from the museum’s café, although it is not necessary to purchase a ticket or a café item to dine here.