Chicago’s 15 Best Rooftops and Patios for Outdoor Eating and Drinking

Take It Outside: Our 16 Favorite Outdoor Dining Spots Around Chicago (Cindy's)

In the interest of journalistic integrity, a full confession: When it comes to the great outdoors, I’m a bit of a princess. Meaning, I don’t do camping. I don’t like outhouses. You will not find me portaging my groceries on a grand canoe trip. And don’t get me started on bugs.

But on a gorgeous summer Chicago day, I will file away my many phobias and dislikes for the greater good of a meal al fresco (albeit with indoor plumbing close at hand, and no random marsh full of mosquitoes nearby). There are glorious outdoor dining experiences to be had in Chicago, and plenty that don’t involve a mouthful of bus exhaust along with your frosé. Here are some of our current favorites.


122 W. Monroe St., Chicago, 312-750-9007

outdoor dining: Boleo
Photo by David Szymanski.

This fabulous indoor/outdoor space is located on the 15th floor of The Kimpton Gray Hotel in the Loop. When the weather is good, the roof is open, and when inclement, the roof is closed. Either way, it’s a party up here (live music Wednesday-Saturday nights), and the food is special. Chef Cory Morris, a veteran of José GarcesMercat a la Planxa, brings worldly finesse to South American favorites like empanadas, ceviche, and anticuchos (skewered beef, shrimp, chicken, and pork get a turn on the plancha). The Pisco Sour always hits the spot, but look beyond to find sparkling cocktails, and some seasonal “garden to glass” offerings. Sit back on your comfy couch and enjoy.

Blue Door Kitchen & Garden

52 W. Elm St., Chicago, 312-573-4000

In back of Art Smith’s genteel Southern spot is a magical garden patio filled with wicker chairs, striped umbrellas, and sunshine (or moonlight, depending on your timing). The Gold Coast has never seemed quite so inviting as when sipping a brunchtime Bloody Mary and devouring an order of Art’s Chicken & Waffles.


12 S. Michigan Ave., Chicago, 312-792-3502

outdoor dining: Cindy's
Photo courtesy of Chicago Athletic Association Hotel.

No roundup of outdoor spaces would be complete without this Chicago Athletic Association Hotel rooftop resto and its spectacular views of Millennium Park, the Art Institute of Chicago, and Lake Michigan. Chef Christian Ragano continues to surprise with his seasonal shared plates, like a recent Asparagus Risotto with spring peas, truffle cheese, and green garlic vinaigrette, or the Grilled Cobia Loin marinated in chili yogurt and served with yellow lentils and a coriander raita. New Beverage Director David Mor has outdone himself with his “Potions & Elixirs,” but his modern riff on the classic French 75 cocktail, the Scoby Snack, is a stunner: Citadelle gin, kombucha, grapefruit, and sparkling rosé — truly, all of my favorite liquids in one place.

Fig and Olive

104 E. Oak St., Chicago, 312-445-0060

Dining out on the lovely terrace overlooking the tree-lined shopping mecca of Oak Street, it’s easy to imagine yourself in the South of France, enjoying a bottle of Provençal rosé, sharing a few Mediterranean-inspired appetizers (the Signature Crostini, Octopus Carpaccio, and Plateau de Fruits de Mer will do the trick nicely), and talking about the balmy weather.

Five and Dime

1026 Davis St., Evanston, 847-869-4343

Dan and Laura Kelch had a genius idea when rebooting their beloved LuLu’s and Taco Diablo restaurants. What about a rooftop oasis, three floors above Evanston’s Davis Street, open to the sky? Yes, please. Visit the game room with giant Jenga and ping pong, borrow a Scrabble game from the bar, or just hang out with friends, soak up the sun, and munch on nachos, tuna poke, or a really terrific burger. Bring sunscreen.

Homestead on the Roof

1924 W. Chicago Ave., Chicago, 773-332-2354

Best of 2018: Homestead on the Roof
Photo courtesy of Homestead on the Roof.

When they say “fresh and local,” they aren’t kidding. Here, they’re picking vegetables and herbs on the rooftop and using them in your salad. That’s fresh. And Chef Jesse Badger knows how to make the most of his ingredients, which shine in dishes like his “Caprese” (tomato sushi with chrysanthemum pesto), or an English Pea Velouté with Meyer lemon and crème fraiche. The Coal-Charred Aparagus with Fried Hollandaise and Togarishi spices is a dish I’ve been rolling over in my mind since I first tasted it.

Honey Butter Fried Chicken

3361 N. Elston Ave., Chicago, 773-478-4000

outdoor dining: Honey Butter Fried Chicken
Photo courtesy of Honey Butter Fried Chicken.

This Avondale favorite has a big backyard patio that pretty much demands that you eat your weight in glorious fried chicken, corn muffins, and honey butter, and that you have a nice cold beer to keep it all company in your stomach. I also love that they pay their staff a living wage, including health insurance, paid parental leave, and more, and that they use only compostable and biodegradable packaging, and recycle and compost restaurant waste. Now that seems worthy of your support, right?


7931 Lincoln Ave., Skokie, 847-674-8100

Downtown Skokie can feel a little industrial but walk back into this charming outdoor patio and be glad you’re outdoors. The food is Nuevo Latino, with flavor elements of Mexico and Central and South America, and there’s plenty to love, whether you’re an herbivore or carnivore. Don’t miss the branzino with fennel-parsley-lemon gremolata, fresh veggies, and caper-serrano vinaigrette if it’s offered, and I always love the Margarita Roja with the added herbal/floral boost of HUM Liqueur.

Mon Ami Gabi

2300 N. Lincoln Park West, Chicago, 773-348-8886 

outdoor dining: Mon Ami Gabi
Photo by Christina Slaton.

This archetypal French bistro has been around awhile, but I never tire of their perfect Steak Frites, done Au Poivre style, of course. Ditto the Frisée, Kale and Warm Bacon Salad with a luscious soft-boiled egg on top to stir into the dressing. As for the outdoor patio, a wrought-iron fence adds visual appeal, as do the stone-topped tables and bent-cane chairs. Lincoln Park is just across the street, and all is leafy and green. This calls for a toast! Where’s the Veuve?


101 E. Erie St., Chicago, 312-667-6796

The oh-so-hip Conrad Hotel has a rooftop secret, and I’ve got to share it with you. Noyane (which means “hidden roof” in Japanese) is your chance to dine on sushi in the sky. Patio lights and stars twinkle above, while Chef Richard Sandoval’s stunning presentations sparkle on the plate. The Sticky Ribs, flavored with Vietnamese nuac chom, are Wet-Nap worthy, to be followed immediately by a Spked Snowball, adult-style fluffy shaved ice in flavors like Bourbon Peach and Passion Fruit Gin. That will definitely get you in the mood.


201 E. Delaware Place, Chicago, 312-280-0700

outdoor dining: Pelago
Photo courtesy of Pelago.

You’ll find a spacious terrace ringed with blossoms outside of Pelago, just a few blocks off Michigan Avenue’s shopping strip, but worlds away in terms of atmosphere. This is a place to savor Chef Mauro Mafrici’s handmade Italian pastas (the Taralli al Pomodoro e Rucola, plump ricotta dumplings with arugula and ripe, fresh tomatoes, is summer perfection), salads, and expertly prepared secondi piatti (entrees). Linger over a limoncello or a strong, dark espresso.

Piccolo Sogno

464 N. Halsted St., Chicago, 312-421-0077

Chef/owner Tony Priolo has truly created a “little dream” in this extensive backyard patio, and wow, does it deliver all the summer feels. Lush plantings and trees, twinkly lights, and beautiful, authentic Italian food, including house-made breads and pizza dough? Magnifico. This place has it all.

Tied House

3157 N. Southport Ave., Chicago, 773-697-4632

outdoor dining: Tied House
Photo by Ryan Beshel.

Chef Debbie Gold is back where she belongs: Chicago. After many years away in Kansas City winning James Beard Awards and raising a family, she’s returned to open this new restaurant in the Southport corridor. Her seasonal food is both visually stunning and thought-provoking, but most importantly, straight-up delicious. And the sunlit, trellis-covered (and dog friendly!) terrace, tucked in the nook between the restaurant and Schubas next door, has comfortable leather benches, a huge fireplace, and a sense of calm. If you don’t order the Bread Service (Parker House Rolls, Seeded Rye, and Honey Oat Porridge Bread) with the Chicken Liver Mousse and Green Tomato Marmalade, I don’t know that we can be friends.

Union Squared

1307 Chicago Ave., Evanston, 224-714-3100

This hidden beer garden, replete with cornhole games and Detroit-style square pan pizza, is an Evanston favorite. Follow the signs through the narrow alley a few steps north of the restaurant on Chicago Avenue, order some local beer (Sketchbook and Temperance are hometown heroes), and delight in this suburban oasis.

The Warbler

4535 N. Lincoln Ave., Chicago, 773-681-0950

Just off Lincoln Avenue and next door to sister restaurant Gather, you’ll find The Warbler, a smash right out of the gate. Their extensive patio seats 120, and the customers are sharing Pork Belly Nachos with tomatillo salsa and black beans, Korean-style chicken wings, ponzu-glazed Crispy Cauliflower with roasted cashews and pickled red onions, and Chicken Sausage Flatbread with garlic cream and manchego. They’re nursing bird-themed cocktails (the Parakeet, a vodka cocktail with celery juice, Douglas Fir Liqueur, and lemon, is mad refreshing) and having a fine old time. Don’t you want to join them?

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Julie Chernoff, Make It Better’s dining editor since its inception in 2007, graduated from Yale University with a degree in English — which she speaks fluently — and added a professional chef’s degree from the California Culinary Academy. She has worked for Boz ScaggsRick Bayless and Wolfgang Puck (not all at the same time); and sits on the boards of Les Dames d’Escoffier International and Northlight Theatre. She and husband Josh are empty nesters since adult kids Adam and Leah have flown the coop. Rosie the Cockapoo relishes the extra attention.