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Chicago on a beautiful summer day is quite literally perfection. And because those beautiful summer days are short-lived, Chicagoans embrace them to the fullest, which means frequenting restaurants where the outdoor atmosphere is as vibrant as the cuisine. Here are the best al fresco dining spots in Chicago to check out this summer.


Cindy’s, 12 S Michigan Ave.

Cindy’s is consistently named a must-visit rooftop restaurant in Chicago, and for good reason. Located atop The Chicago Athletic Association Hotel, the gorgeous open-air terrace is unbeatable for experiencing the beauty of Chicago while enjoying upscale seasonal fare and a delicious rotating menu of craft cocktails.


Piccolo Sogno, 464 N. Halsted St.

Piccolo Sogno serves up rustic Italian fare and an all-Italian wine list in a gorgeous patio setting reminiscent of old-world Tuscany. It’s perfect for a romantic summer dinner or a leisurely lunch under shady trees.

River Roast, 315 N. LaSalle St.

River Roast is the perfect spot to enjoy a lively brunch or dinner while taking in the beauty of Chicago’s bustling riverwalk.   


Green River, 259 E. Erie, 18th Floor

Green River is a Michelin-starred restaurant that offers award-winning upscale American fare, beautifully crafted cocktails, and some of the most stunning views of the city from its 18th floor terrace.

Homestead on the Roof, 1924 W. Chicago Ave.

Homestead on the Roof is a cozy, innovative farm-to-table restaurant tucked away on the rooftop of Roots Handmade Pizza. Homestead takes the farm-to-table approach to heart, as their menu reflects a rotating seasonal harvest from their adjacent 3,000 square-foot organic garden.   


Zed 451, 739 N. Clark St.

Zed 451 offers modern churrascaria cuisine in a sleek urban rooftop setting with killer views of downtown Chicago. Their weeknight rooftop happy hour is the perfect way to kick off a summer night with small bites and delicious drinks.


Parson’s Chicken and Fish, 2952 W. Armitage

Parson’s Chicken and Fish is a sure thing for those leisurely summer weekend days. Relax, kick back, and linger over comfort food at its best in a hip, outdoor setting. And by comfort food we’re talking fried chicken, pimento toast, hush puppies, pie, and ice cold beer. You may want to nap afterwards, but that’s what summer is for.

The Dawson, 730 W Grand Ave.

The Dawson is a contemporary restaurant serving new-American cuisine in a modern industrial setting. The outdoor patio is spacious and comfortable, offering lots of cozy seating under string lights with added ambiance from an outdoor fireplace. The casual elegance makes it a great outdoor destination for cocktails with friends after work or a date night.


RM Champagne Salon, 116 N. Green St.

The gorgeous patio at RM Champagne Salon is located off of a small cobblestone alleyway in the West Loop, which adds to the romantic quality of this European-inspired champagne bar. There’s a menu of small bites and an impressive drinks menu. They’re open Friday and Saturday until 2 a.m. with a special late-night menu, so it’s ideal for stealing away with a new (or old) summer love.

Little Goat Diner, 820 W. Randolph St.

Little Goat Diner is the causal wing of Stephanie Izard’s (of Girl and the Goat fame) restaurant empire, and the rooftop deck at Little Goat offers guests a fun and relaxed atmosphere to enjoy elevated diner cuisine in the heart of the city. They open daily at 7 a.m. if you want to beat the midday heat.


Big Star, 1531 N. Damen Ave.

One word to sum up the experience of dining on the outdoor patio at Big Star in the summer: poppin’. Part taco joint, part house party, patrons enjoy a straightforward and delicious menu of tacos, whiskeys, and margaritas all set to the soul sounds of Big Star’s house DJs. It’s also a great spot for watching the lively cross-section of hip 20-somethings and diverse array of folks who just love good tacos.

Gather, 4539 N. Lincoln Ave.

Gather offers a lovely secluded patio where diners can enjoy New American fare in a warm and inviting atmosphere in the city’s historic Lincoln Square neighborhood. They also serve up one of the best brunches in the city and a rustic Sunday family dinner menu.  


Bridge House Tavern, 321 N. Clark St.

During the summer months, Bridge House Tavern spills out onto an expansive outdoor patio situated on the Chicago River. Enjoy the people watching and skyline views over New American comfort food and a vast drink menu.

Ada Street, 1664 N. Ada Street

The intimate patio at Ada Street is a great choice for dinner with good friends or a relaxed date night. The atmosphere is relaxed, and you can enjoy New Mediterranean-American inspired small plates under the twinkle of Edison-bulb string lights.