The Best Chicago Rooftops For Eating & Drinking

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 impress - like visiting colleagues, or your soon-to-be sister-in-law who kind of hates the city.

Tanta is always a fun restaurant with a lively scene. 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 busy sidewalk while trying to ignore the tourists and buses going by. This place is perfect for a weekend date, or even a nicer dinner during the week.

The rooftop patio at Taxim feels a little like the kind of place where Peter Parker (a.k.a. Spiderman) might bring a date. It’s surrounded by brick walls from adjacent buildings, and the fact that they’re uplit somehow makes them seem very climbable. There’s a nice outdoor bar area, and the whole space has an upscale 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.

When you have a corporate card and out-of-towners you want to entertain, Gibsons Italia is a good power move. It looks and feels expensive, and has an fantastic view of the Chicago River. This is particularly true on the third floor, thanks to its retractable roof. During the winter, there’s even a fireplace you can sit around while planning either the company picnic or a hostile takeover. Just don’t let the “Italia” in the name distract you - as far as food goes, your best bet is to stick with the steaks, or anything else that looks like it belongs on the menu of the original Gibsons steakhouse.

Thanks to Celeste, it’s possible to hang out in a secret garden in River North. The rooftop bar here has ivy-covered brick walls, and is full of plants and marble tables. This place is basically an oasis floating above the hordes of bars and tourists on Hubbard Street. Come here for cocktails with friends before a night out downtown, or for a special occasion.

When you first walk into Cindy’s, you’ll wonder why you don’t spend more time here. This place has beautiful views overlooking Millennium Park and Lake Michigan, and overall it’s great 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 French toast, or come for dinner and order a platter of New York strip. The food won’t blow you away, but the atmosphere makes up for it.

River North has a lot of loud and crowded spots, and that makes us really appreciate hanging out on the relaxed rooftop at Bernie’s Lunch & Supper. The tables here are far enough apart to make it feel spacious, and you’ll be able to get a seat at the large outdoor bar if you’re just having a drink after work. As long as you’re doing that, you might as well get their excellent burger - it’s number 15 on our Burger Power Rankings.

A lot of restaurants talk about serving “farm to table” food, but Homestead On The Roof takes this concept one step further. 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 to riding a hay wagon through West Town as you’re likely to get, so come when you want to feel like you’ve left the city.

Devereaux is good to know about for a few reasons. It’s the rooftop bar at the Viceroy hotel, which means you can get snacks and small plates from Somerset, one of the best restaurants in Chicago. Plus, it has a four-foot-deep swimming pool you can float around in. So basically, this is where you come when you want to pretend you’re at a hotel in Vegas, but with better food.

One of the drawbacks of sitting on a rooftop downtown is that you can’t see the whole skyline, because you’re technically in it. This isn’t the case at Cabana Club, the rooftop bar on top of a high-rise hotel (The Robey) in Wicker Park. Enjoy the skyline view while you have a cocktail and some light snacks like cucumber dip or ceviche. It’s a very good way to spend some time before disappearing into one of the street-level restaurants in the neighborhood. (There’s a small pool here, too, but it’s not the main attraction.)

Pearl’s has 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.