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 13 best rooftops in Chicago, for all sorts of socially-distanced occasions.
This is the low-key rooftop restaurant on top of Pacific Standard Time in River North. The Laurel Room is from the same team, which means you’ll find the same California-inspired seasonal menu. As a bonus, since the rooftop is covered, you can sit outside even when it’s raining.
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.
You might know Joy District as the loud bar on top of Parlay in River North, because it is. But now this rooftop bar serves food and has couches and high tops so you can hang out for a while.
Utopian Tailgate opened late last year in Old Town, and we hardly had any time with it before both Chicago winter and the shutdown started stealing our joy. This 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.
After a lot of delays (this project started in 2015), Nobu has finally opened in the West Loop. 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.
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.
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. Make sure to order more tortilla chips - they’re very good and you’ll want extra.
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 mushroom tostadas, pork belly bao, and grilled jerk shrimp. 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 (yes, they’re still 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.
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.
We really appreciate hanging out on the relaxed rooftop at Bernie’s Lunch & Supper. The tables here are far enough apart to make it feel extra spacious, and they just expanded their awning. They also still take reservations even when it rains, and more importantly, your hair won’t get wet. Also important? They have one of our favorite burgers in Chicago.
Pearl’s has another one of the best low-key rooftops in the city. It’s hiding up in Edgewater, so it doesn’t get nearly as busy as the ones downtown. And while it’s not actually too many stories off the ground, the roof still has a fantastic view. The food here is (as you may have guessed from the name) Southern, so you’ll find things like po’boys and jambalaya, plus some very good barbecue. All of those things go well with a Hurricane - which is exactly the kind of cocktail you should be drinking.