As long as you pick the right one, being on a rooftop in Chicago is great. You get a view of the city, plus a breeze that will save you from the unrelenting summertime humidity (which we all know is just the pent-up energy from frustrated snow). But a rooftop with bad drinks or a boring view is about as much fun as sitting in a plane on the tarmac—and you definitely don’t have time for that this year. Here are the best rooftops in Chicago, for all sorts of occasions.
THE ROOFTOPS
Yes, Aba can be kind of a scene. Thankfully it’s one with great food and a huge rooftop patio full of firepits and comfortable couches. And as with its sister restaurant Ema, a lot of things (like the hummuses and spreads) on the Mediterranean menu are meant to be shared.
Cabra is filled with plants, natural light, and has a great view of the West Loop. They also serve some very good Peruvian food. The best things here are the ceviches—the bass with leche de tigre and the duck are great)—and the shrimp tacu tacu which comes on a delicious crispy rice cake.
It’s not a high-rise, but this place is great for when you’re afraid of heights or don’t want your sexy windblown look to be too realistic. Lonesome Rose, a Tex-Mex restaurant in Logan Square, has a rooftop patio that’s only one story up, so you get a nice breeze, a solution for your Vitamin D deficiency, and the chance to eat some tasty fish tacos and queso outside.
Bar Avec is the rooftop bar on the eighth floor above Avec River North, which opened in the former Pacific Standard Time space . And it’s a perfect low-key rooftop option that has great food, and won’t involve a gazillion tourists. The rooftop is shaded and full of plants and trees, and has a great view of downtown. It also has a separate Spanish-inspired menu. Food options here include small plates like mussels escabeche, crudos, and entrees like fideo noodle paella. And in case you were wondering: yes, they have the bacon-wrapped dates on the menu.
Eleven Eleven is an upscale wine bar with great food that (despite being in the West Loop) manages to be relatively relaxed. You’ll find options like shrimp and grits, cacio e pepe, and BBQ cauliflower “burnt ends” that are truly delicious.
Aire Rooftop Bar
Aire is on top of the Hyatt Centric in The Loop, and since it’s on the 24th floor, it’s unsurprising that the views are incredible. Along with serving cocktails and some local beers (like Half Acre and Revolution), there’s a short food menu with small bites like cheese and charcuterie, flatbreads, and sliders. Come here with anyone visiting the city who you want to impress with a panoramic view of downtown.
I|O Godfrey
The spacious rooftop bar at the Godfrey has lots of couches that are perfect for hanging out with your friends over drinks. Plus, it has a retractable roof so you don’t need to worry about bad weather ruining your plans.
Utopian Tailgate
This Old Town bar reminds us a lot of a rooftop version of Paradise Park—meaning astroturf, lots of colorful patio furniture, and things like swing sets. Their food and drink menu is tailgate-themed, so you can find things like nachos, pizza, and skewers.
Not only does Etta have great food, but it also has a great rooftop patio. This place serves delicious housemade pastas and pizzas, plus other dishes (like vegetables and pork shoulder) made in a wood-fired hearth. Come here for dinner with co-workers that (until recently) have only existed as squares on Zoom, a casual date night, or catching up with friends.
Kennedy Rooftop
The Kennedy is on top of the Hyatt in Wicker Park, and since you’re not literally in the skyline, you have a nice view of downtown Chicago. It also has a long menu full of cocktails and bar food, and plenty of tables and couches spaced far apart for social distancing.
Whiskey Business
This is another rooftop in Wicker Park, and at 3,000 square feet, is very large. Whiskey Business also has other things to do besides eating and drinking. On Mondays and Wednesdays they have movie night, and on the weekends they serve bottomless brunch.
The rooftop patio at Taxim is great. It’s surrounded by brick walls from adjacent buildings, there’s a nice outdoor bar area, and the whole space has a cozy feel. Plus, the Greek food is consistently good - you should make sure to get a pastry appetizer (like leek and goat cheese in homemade phyllo), and any dish that includes lamb.
Thanks to Celeste, it’s possible to hang out at a secret garden in River North. The rooftop bar is surrounded by ivy-covered brick walls, and full of plants and marble tables. Come here for cocktails with friends before dinner downtown, or just to hang out.
The Rooftop At Nobu Hotel
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After a lot of delays (this project started in 2015), Nobu finally opened in the West Loop in 2020. This rooftop bar is 11 stories up on top of the hotel, and along with a long list of sake and cocktails, they also serve Japanese small plates and sushi.
Vu is a rooftop bar on the 22nd floor of a building near the McCormick Center. And since it has both firepits and retractable windows, it’s good for the occasional 53-degree Chicago summer day. There’s a long menu of small plates, with dishes like popcorn shrimp, crab dip, and flatbreads. It’s all fine, but our favorite activity here is to drink and be glad we’re not going to the Morningstar Investment Conference this year.
Take your average Chicago block party and plop it on a rooftop deck, and you have Reggies in the South Loop. This casual bar and music venue (though right now they’re not hosting shows) has cold beer, burgers and wings. And unlike your neighborhood block party, the rooftop has very little probability of screaming children. What it lacks in view (overlooking a deserted section of State Street and Cermak) it makes up for in a relaxed and fun atmosphere.
Cerise is the bar on the 26th floor of the Virgin Hotel in the Loop, and it’s exactly what you’re looking for in a sceney downtown rooftop: great drinks, a short menu of just-fine snacks (like avocado toast and a fried chicken sandwich), and fantastic views of the city.
This is a fancy spot at the top of The Peninsula, a luxury hotel near Michigan Ave. Because of its location, it has a great view of the Magnificent Mile, which makes it an ideal place to take out-of-towners. You’ll find small plates like foie gras-filled bon bons and marrow “poppers” (which are basically tater tots filled with bone marrow). Come here and eat some expensive bar food with anyone you’re trying to impress - like visiting colleagues, or your soon-to-be sister-in-law who kind of hates the city.
Tanta is always a great restaurant, but it’s best in the summer when you can hang out at the rooftop bar. Not only can you eat tasty Peruvian food like cebiches and skewers, but you can also avoid the typical outdoor dining situation in River North—i.e. sitting on a sidewalk while trying to igore the garbage trucks going by. This place is perfect for a weekend date, or even a nicer dinner during the week.
When you first walk into Cindy’s, you’ll be grateful they reopened after closing last July. The restaurant on top of the Chicago Athletic Association hotel has beautiful views overlooking Millennium Park and Lake Michigan, and overall this is a great place for groups, because the menu has dishes meant to be shared among three or four people. Come here for brunch and get a giant serving of blueberry pancakes, or a platter of linguini with clams for dinner. The food won’t blow you away, but the atmosphere makes up for it.
Raised is a cute flower-box-lined rooftop right on Wacker and State with a great view of the Chicago River. This spot is low key, with a menu of elevated bar food items like tenderloin sliders, lobster rolls, and charcuterie. Come here when you don’t want to worry about being blown away by gale-force winds.
The Woodlawn
The Woodlawn (located in...wait for it...Woodlawn) has rooftop seating, along with private party domes you can reserve for $125 per person, and they seat two to six people. The reservation includes a three-course meal and you can still BYOB.
A lot of restaurants talk about serving “farm to table” food, but Homestead On The Roof takes this one step further. Meaning they grow their own vegetables and herbs in their rooftop garden, and in the summer that garden doubles as an outdoor seating area. It’s as close tos riding a hay wagon through West Town as you’re likely to get. In other words, this is the kind of rooftop dining feels like a real day trip outside the city. Just check their Instagram to see when they’re officially open for the season.
