Chicago Restaurants With Luxe Outdoor Dining Spaces

As most Windy City natives would agree, the dog days of summer are very sweet, but often too short. While locals can enjoy Chicago’s fleeting heat by a rooftop pool or at a park, there’s nothing quite like the city’s summer-friendly outdoor dining scene. Decadent fare, cooling libations, and a warm climate make for an ideal seasonal send-off. Toast to the end of summer at these five memorable eateries that champion alfresco dining.

The Dawson

The Dawson

Get your boozy outdoor brunch on one final time at this beloved gathering place in the Fulton River District that is dishing up sinfully delicious seafood and relaxed vibes out on their radiant patio. The expansive, bi-level resto makes Sunday morning reminiscing easy with tasty breakfast offerings and thoughtfully crafted bloody mary’s. Opt for a side of September sunshine with their avocado toast as you look back on exciting summer travels.

Contact: 730 W Grand Ave., 312-243-8955



This teeny open-air space sets the scene for a charming evening. Cozy up to pleasant temps and a glass of vino next date night at this intimate eatery that serves enticing shareable plates and superb wines on their dimly-lit terrace. Let romance fill the warm air as you bid adieu to summertime over veggie-centric dishes, like their summer squash, crispy cauliflower, and marinated eggplant.

Contact: 4539 N. Lincoln Ave., 773-506-9300


NoyaneSun-kissed globetrotters who are feeling post-vacay blues can seek refuge at this sky-high restaurant that boasts a sleek outdoor lounge, dining, and bar space. Not only does The Conrad Hotel’s rooftop restaurant provide refreshing skyline views, but the towering sushi and sake destination also offers impressive ice-cold cocktails and cooling Japanese cuisine. Recall roasting summer temps over Chef Richard Sandoval’s famed A5 black wagyu beef: grilled to perfection on a sweltering hot stone.

Contact: 101 East Erie St., 312-667-6796

Piccolo Sogno

piccolo sogno

It’s only appropriate that Piccolo Sogno—Italian for “little dream”—boast a lush, garden-like atmosphere that gives off serious Alice in Wonderland vibes. A dreamy dining space like this is best enjoyed while the weather’s still nice enough to don sleeveless ware. Sprawling trees, delicate string lights, and ivy-clad walls set the scene for a magical meal.

Contact: 464 N. Halsted St., 312-421-0077



Cheers to summer in sweet seclusion at this famed Michelin Starred restaurant that’s fitting for an upscale date or chic gathering. While Boka’s stunning interior gives guests plenty to brag about, nothing quite compares to a world-renowned meal beneath the stars—sans people heaters, of course.

Contact: 1729 North Halsted St., 312-337-6070