This summer hang out at the only spot in town that's got cabanas on the beach. Now that Grass Fed partner Josh Schonfeld has revamped the food and beverage program at Caffe Oliva, you can enjoy fresh Mediterranean fare like grilled calamari and Greek salads along with burgers and lollipop wings. Wash that all down with buckets of beers, mojitos and spiked lemonade cocktails while enjoying stunning views of the beach and Chicago skyline.

If you’re looking for a quiet spot to relax then you’ve come to the wrong place because the party never stops at Castaways. Located on the always-packed North Avenue Beach, this multi-level oasis features appetizers, burgers, salads, sandwiches and more as well as a full bar and various house cocktails. Live entertainment keeps the crowds coming.

Surround yourself with sand, sun, water, volleyball courts and great food and drinks at The Dock. Always a popular hotspot, munch on some chips and guacamole and try a number of sandwiches, burgers and dessert options. A full bar and live music keeps the good times going into the night.

Located at the edge the Chicago River, Fulton’s on the River has great downtown views especially along the spacious outdoor cafe. This classic seafood and steakhouse offers everything from oysters and Alaskan King crab legs to bone-in rib-eye and filet mignon.

Speaking of Fulton's on the River, try Bridge Bar, located inside, for a drink after work. Enjoy views of the river and some of their unique cocktails which may feature some of their Slim Jim-infused bourbon.

The only thing better than outdoor dining season is outdoor dining season with booze, food, and ping-pong tournaments. At Japonais, you can enjoy the warm summer weather, grab a seat in a cabana and sip on some refreshing craft cocktails before you beat all your friends in a crucial match of pong on the riverside patio.

For a great summer romance, take your beau to North Pond, located inside the quaint former ice skating shelter next to the Lincoln Park pond. With dramatic views of the Chicago skyline, the lake steps away, and a James Beard Award winning chef at the helm, you're pretty much guaranteed a second date.

Tucked away inside the South Shore Cultural Center, the Parrot Cage is located between the beachfront and the greens of the South Shore golf course. The restaurant is operated by the Washburne Culinary Institute and offers contemporary American cuisine inside an elegant dining room. In addition to the $30 prix fixe special on Wednesday and Thursday nights, experience a Sunday brunch buffet filled with classics.

Get comfortable because Lake Shore Cafe serves comfort food all day for breakfast, lunch, and dinner. With sweeping views of Chicago's lakefront, it's a great place to spend a Sunday brunch or a Friday night for live jazz and a seafood buffet.