05/02/2011 02:43 pm ET Updated Jul 02, 2011

Chicago Outdoor Dining: Five Great Al Fresco Spots

Even if Windy City weather wants to fake us out with overcast, moodswinging days, eventually, we'll lure the sun to stay for a while. When it does, be ready for a multitude of patio chairs and tables around the city to be filled with those who want to take in some summer rays with their drinks and food. We found these five great spots to dine al fresco, all with different vibes and eats but all eateries that share an eagerness to embrace fine weather.

The Southern: Watch the cars jammed on North Avenue from the patio at The Southern while being glad that you're not stuck in one of them. Even the inkling of a warm day brings the Wicker Parkers and Bucktowners out for beer and comfort food on the metal black tables and chairs at The Southern, which has prime open-air, people-watching space. While relaxing outdoors, cut into fried green tomatoes, shrimp n' grits or a Piggly Wiggly (consisting of a can't get-more-southern pork shank, carrot puree, pickled raisins, collard and smoked bacon). Don't miss the appetizers, which include Johnny Cakes made with applewood smoked pork, or the Mac Truck Special, a nod to the creations of Executive Chef Cary Taylor's mac and cheese food truck. If you're hanging at The Southern with a big group of buddies, share an entire punch bowl of Southern cocktail, a concoction of Beefeater gin, Prosecco and fresh lemon that serves 10 to 15 people.
1840 W. North Avenue; 773-342-1840

Heartland Cafe: This Chicago institution was at the forefront of organic dining and remains a beloved spot for activists of all kinds. Heartland Cafe started 35 years ago with a mission to serve "good wholesome food for the mind and body," and as the weather warms, the eatery makes an effort to get its produce from local farmers and sometimes grows some of its own. Brown rice, salad and several veggies are organic the whole year, and the cafe's chicken is always either organic or Amish-raised. As expected, even the carryout containers can be composted. But in addition to a holistic mission and a sustainable attitude, Heartland Cafe has loads of atmosphere, too, regularly bringing in folk bands, jazz musicians and singer-songwriters, who all enhance the laid-back environment.
7000 N. Glenwood; 773-465-8005

Piccolo Sogno: The restaurant may translate to "little dream" in Italian, but fortunately for Chicagoans who love to dine al fresco, the little dream at Piccolo Sogno includes a huge patio. A large wooden platform rises off the ground at the River West restuaurant, accommodating dozens of comfortable yet contemporary chairs for patrons who want to enjoy some outstanding Italian food outside. Piccolo Sogno keeps it flavorful yet accessible, with lunch entrees all running under $20, including dishes like tortellini stuffed with artichokes and buffalo milk ricotta, braised oxtail and a medley that includes grilled octopus; dinner, meanwhile, stays under $30 for entrees and encompasses dishes like grilled ribeye and cornish hen.
464 N. Halsted; 312-421-0077

Five Star Bar: Sometimes you just want a tasty burger under open skies, and that's what Five Star Bar offers. Five Star actually doesn't wait until the weather is summery to let in fresh air, as evidenced by a recent cloudy Saturday when the West Town spot threw open its wall of floor-to-ceiling, European-style windows. When you're taking in that Chicago air, chomp on the Five Star burger, which comes with eight ounces of angus beef, bacon and a fried egg. Or try the Verde, with its roasted green chilies and pico de gallo. For the herbivores, Five Star serves up chopped salad and a veggie burger topped with jalapeno mayonnaise.
1424 W. Chicago; 312-850-2555

Zapatista Cantina: Sip sangria and margaritas under an orange awning at Zapatista Cantina. Perched on Wabash in the South Loop, Zapatista's patio embraces drink lovers with an expansive cocktail and wine menu that includes the Million Dollar Margarita, served with Don Julio Reposado tequila and Grand Marnier. Complement those drinks with appetizers like Dos Ceviches, a tasting of Zapatista's citrus shrimp and crabmeat ceviche and its coconut-lime flavored yellowfin tuna ceviche. For entrees, chow down on Fajitas de Molcajete, which can be ordered with tilapia and filet mignon and, as the name implies, come served up in curving food tools of dark stone.
1307 S. Wabash; 312-435-1307