Solid food and drink specials every day, and the patio is a great place to hang and listen to a good mix when the weather is nice out.
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.
Add this to the list of downtown rooftop spaces with a hip, modern terrace atop the Raffaello Hotel. The menu features a mix of seasonal cocktails along with a focus on bourbon and whiskey.
Enjoy the view from the rooftop patio or the glass-enclosed space in the winter, with comfy couches, high-top tables and bar seating, it's a big draw for Erin Hayes' destination-themed cocktails.
Beautiful rooftop lounge, great place to come with a group of friends or a classy drink date
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.
Fireworks in the summertime on Wednesdays and Saturdays @ 10 pm...Very nice view esp. from The Trump Tower Terrace!
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.
Get here early on a summer evening, colonize a big table on the back patio and hold court with several of your fellow beer lovers until the tamale man arrives with reinforcements.
On warm summer nights, the two bars at this multi-tiered rooftop are bustling with Boystown boys. Read more.
The avena (oatmeal) shake is one of the best shakes in the city. BYOB joint. Cash money only. No plastic.
Wonderful, cash-only beer garden above Gene's with an array of delicious sausages and beers.
Great atmosphere, great hospitality. Ping-pong and a gorgeous patio. Sometimes the owner will play chess with you, too.
This place is 1)right on the lake, 2) sells BEER AND WINE, 3) and is affordable (like $7-8 per item). Worth a visit!
One of the best views of Millennium Park. Great food and service. Really busy every day of the week, definitely need an RSVP.
The rooftop here is unmatched in Wicker Park! Large open rooftop with 2 huge TVs. Great for sporting event on a nice summer day!
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.
Nice week night rooftop happy hour. Good drink specials and a great burger
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.
