The Best Outdoor Dining Spots in Chicago

There’s just something about eating outside in Chicago in the summer. Whether your view is of the city below, of the Chicago River, or just of the throngs of people rushing by, it seems that eating outside just makes the food taste better, the beer a little more refreshing. From the Loop to Lakeview, River North to Bucktown, here are some of the top outdoor dining options in Chicago.

Bin Wine Cafe
This Bucktown bistro offers creative small and large plates, and expertly paired wines. In summer, come for thin-crust pizza, a wine flight, and the people-watching on Milwaukee Avenue.

Located in River North, this Brazilian Steakhouse offers a rooftop deck set amongst the area’s high-rises. Though it’s only one story tall, the space is “decked out” to feel like your very rich neighbor’s swanky patio, and the way it puts you eye-level to nearby residences only adds to that feel.

Flatwater has one thing (and, some would argue, one thing only) going for it – its unbeatable location along the Chicago River. The food is nothing to write about (literally) and the service is often absent, but on a sunny summer day downtown, the patio is still packed with people who come just to enjoy the view.

Park Grill
Just west of Millennium Park on Michigan Avenue, the Park Grill offers lunch, brunch dinner and drinks. Salads, sandwiches, flatbreads, burgers, steaks, pasta and fish are among the selections.

DeLa Costa
DeLa Costa offers not just one, or two, but three outdoor dining options – there’s the front sidewalk cafe, the back patio overlooking the Chicago River, and a floating patio on the River itself. Menu options include fresh ceviches, soups and salads, and meat dishes like roasted duck or cured salmon.

River-North celeb hot-spot Sunda offers Asian fusion small and large plates for dinner (plus a new Sunday brunch). The sidewalk patio is perfect for people watching, especially on weekend nights as the club-goers begin to take to the streets.

90 Miles
90 Miles Cuban cafe dishes up tasty Cuban specialties indoors at on the small outdoor patio, with the added benefit of being BYOB. So bring a few beers or the makings for some Sangria or Cuba Libres and sip under the sun or stars for less.

The Publican
Located in Fulton Market, the Publican is all about the meat….and oysters….and beer. If these three things are among your loves, and you don’t mind paying more for hard-to-find quality items like suckling pig, veal brain sausage, the freshest oysters, and imported beers, this is the place for you. Dine inside at the lively communal seating or outside on the intimate patio.

The Southern
This Wicker Park spots has had many incarnations in the past, but it seems like the Southern may be here to stay. With a small but authentic menu of friend chicken, fried green tomatoes, southern poutine, crab cakes, and other fixings, it also offers several southern cocktails and an extensive Bourbon list. There is a sidewalk patio and a swanky upstairs roof deck, complete with gauzy-draped cabanas perfect for lounging on a summer night.

Big Star (no website 1531 North Damen Avenue)
Chef Paul Kahan goes super-casual with this taco joint in an old filling station. The space is sparse, it’s cash-only, and they don’t take reservations (just stand in line to put your name on the list and then belly up to the bar and wait for the host to call your cell) but the food, and the sprawling outdoor patio are worth the wait.

Just drinking? Check out this list of best rooftop bars.

Photos by Bucky Skeel, jmenard48