Roof at the Wit Hotel seats 150 in its open-air portion and 150 indoors, but even on chilly days, the place fills up quickly. Read more.
Picnic tables and a great whiskey selection make this teeny rooftop, overlooking a fairly blah section of the city, a laid-back spot to catch some sun. Read more.
A 12th-floor perch is sleekly contemporary, offering glowing cube tables and a menu of burgers, sandwiches and light bites. Read more.
Besides boasting a rooftop that features tables made from reclaimed barn doors, the spot also has a menu with some pretty good eats. An all-Midwestern beer selection helps wash it all down. Read more.
Congratulations, you've found one of Esquire's Best Bars in America. With 150 beers on tap, including Trappist ales and mead, try to order something other than a Stella Artois. Read more.
On warm summer nights, the two bars at this multi-tiered rooftop are bustling with Boystown boys. Read more.
This bistro-terrace combo sits on the third level of the Loews Hotel. The 9,000-square-foot space seats about 280 and offers a highly underrated view of the city. Read more.
Sitting on the 26th floor of the Virgin Hotel, Cerise is considered the “cherry on top” of the Loop hotel. It’s one of five dining and drinking options in the hotel, but definitely has the best view. Read more.
This flavorful lunch spot offers an incredible midday menu, which includes filling options like a juicy steak salad and a delicious cheeseburger with optional "thieves-thick" bacon. Read more.
Nestled amongst the vines, diners can perch on Victorian wrought-iron furniture, admire antique bird cages and sip drinks like the "Midlife Crisis," a combo of Mezcal, coconut, and pineapple. Read more.
This low-key rooftop is filled with picnic tables, giant umbrellas and the smell of sausages on the grill. They've got a half German, half American draft program, and a great food menu. Read more.
Fountainhead boasts one of the chillest rooftops in town. It's sunny, it's got a small food menu, and there is literally no other rooftop bar in Chicago with a selection of drinks as good as this one. Read more.