Summer in Chicago makes the snow, cold and parking spot dibs all worth it, so take advantage of our beautiful city’s warmest months at some of the top rooftop restaurants while you can. Between downtown classics, Logan Square Tex-Mex and even freshly-made, German-style sausages at a rooftop beer garden, you’re sure to find something you love. Read on for our top picks.
Cabra
Cabra, Top Chef winner Stephanie Izard’s Peruvian-inspired restaurant, is located on the rooftop of The Hoxton Hotel. The Fulton Market hotspot offers an expansive menu with dips, entrees and ceviches, plus a cocktail list that’s perfect for sipping poolside — which is great because right outside the restaurant’s doors is Hoxton’s Instagram-worthy pool. Get there early to grab a drink and sip it outside on a lounge chair. And once you’ve had your fill of rooftop views (is that even possible?), head downstairs for a nightcap at Lazy Bird, the upscale speakeasy in Hoxton’s basement.
200 N Green St, Chicago, IL 60607
Homestead on the Roof
Located above Roots Handmade Pizza’s West Town location, Homestead on the Roof is an intimate spot featuring a farm-to-table pop-up menu (this year’s theme is Portugal) and a large cocktail list. The space — which has a 1,000-square-foot rooftop garden, complete with flowers and a working fireplace — feels more like a magical dinner party than a bustling rooftop, making it the perfect spot for a long, lingering summer dinner. But be sure to make a reservation because Homestead on the Roof is also a highly sought-after private event space, so it’s frequently closed for parties.
1924 W Chicago Ave, Chicago, IL 60622
Lonesome Rose
Lonesome Rose, a Tex-Mex restaurant that’s been featured on the Michelin Bib Gourmand list numerous times and was a finalist for the James Beard Foundation’s “Outstanding Design Award,” offers a second-floor rooftop at its Logan Square location. The massive menu features Tex-Mex classics (think queso, truck stop nachos, tacos and more), plus a breakfast that’s worth waking up early for. But the real star of the show is the drink menu, which features a range of classic Margaritas, frozens, cocktails, beer, wine, spirit-free concoctions and more, making this rooftop the perfect place to spend an hour (or six) this summer.
2101 N California Ave, Chicago, IL 60647
Cindy’s Rooftop
Cindy’s Rooftop is one of those rare restaurants that’s a hit with both tourists and locals looking for a great night out. The beautiful space — located on the rooftop of the Chicago Athletic Association Hotel — has a covered, spacious inside area and a terrace offering unbeatable views of Millennium Park. The restaurant serves lunch, dinner and a weekend brunch, with classics like oysters, roast chicken, branzino and so many delicious desserts, you’ll want one of each. (A Mont Blanc with purple sweet potato cream, a black sesame pavlova and freshly baked cookies? Count us in!) There’s also an expansive cocktail menu with both alcoholic and spirit-free drinks that are perfect for sipping while gazing lovingly at the Bean.
12 S Michigan Ave, Chicago, IL 60603
Bixi Beer
You don’t need to fight the downtown traffic to experience a beautiful rooftop in Chicago, and Bixi Beer is a great example of that. With a view that looks out across Logan Square, this brewpub serves Chinese, Korean and Vietnamese-inspired cuisine, alongside unique house-made beers like Rules of the Rhein, a Kolsch-style ale made with jasmine tea. Don’t miss Bixi’s happy hour, featuring $2 chili oysters, $6 pints and $10 cocktails, available every Sunday through Friday.
2515 N Milwaukee Ave, Chicago, IL 60647
Gene’s Sausage Shop Rooftop Beer and Wine Garden
At this beloved Lincoln Square rooftop, you’ll feel like you’re vacationing in Germany, with long, communal wooden tables, a view of the Square and generous pours of beer and wine. Gene’s also serves a menu of their signature smoked sausages and bratwurst cooked on an open grill, as well as daily specials. The rooftop is popular, so you may have to wait a bit for a table, but it’s well worth it. Be sure to spend time wandering Gene’s two-floor sausage shop and European grocery store downstairs.
4750 N Lincoln Ave, Chicago, IL 60625
Open Outcry
This Southside brewery in Beverly has all the key elements for a great rooftop experience. Expansive seating? Check. A long list of beers? Check. Wood-fired pizza? Check. Ruby the brewery dog, an English Mastiff who keeps an eye on everything? Absolutely check. Spend a summer day trying the beers, chowing down on pizza and having a good — yet responsible — time. After all, Ruby’s watching.
10934 S Western Ave, Chicago, IL 60643
LH Rooftop at LondonHouse Chicago
Located on the 22nd floor of the LondonHouse Chicago Hotel, LH Rooftop’s views of Chicago are better than any postcard. While the star of the space may be the picture (or, who are we kidding, the 4,000 pictures) that you take posing by the view, the restaurant also has a menu of glamorous cocktails, delicious American tapas and incredible mains that will keep you coming back time and again. If you’re up early on the weekend, don’t miss LH’s unforgettable brunch, with dishes like a breakfast burger, lolli-waffles and king crab Benedict.
85 E Wacker Dr, Chicago, IL 60601
Aba
Aba is a Mediterranean restaurant with a strong California influence, and its stylish rooftop — complete with lush greenery and comfortable couches — pays homage to that. The Fulton Market go-to serves both dinner and weekend brunch, with can’t-miss dishes like smoky garlic hummus, whipped feta spread and creme brûlée pie, plus hard-to-find wines and spirits from the Mediterranean region. Not sure what to do during Chicago’s nine months of non-rooftop weather? Aba has you covered — the rooftop is enclosed from the elements in the colder months, making it the perfect spot no matter the time of year.
302 N Green St 3rd Floor, Chicago, IL 60607
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Taste the flavors of the South Asian subcontinent close to homeBar Avec
Bar Avec’s eighth floor rooftop serves cocktails and food in a casual, “come as you are” atmosphere, making it the perfect spot for a summer afternoon hang with friends. The restaurant is inspired by coastal Spanish and Portuguese towns and has a varied wine list, delicious shareable plates (that, frankly, we won’t blame you for keeping all to yourself) and a dessert menu that includes homemade Nutterbutters.
640 N La Salle Dr 8th floor, Chicago, IL 60654
Nobu
It’s practically illegal to write a list of Chicago rooftop restaurants and not include Nobu. The Japanese restaurant is open for dinner from Wednesday to Sunday, with brunch available on the weekend. While the menu is pricey (it is Nobu, after all), it’s worth it. Don’t miss the black cod miso, yellowtail jalapeño and expansive list of rare tequilas.
155 N Peoria St, Chicago, IL 60607
The Up Room at The Robey Hotel
Located on the 13th floor of The Robey Hotel, The Up Room has unbeatable views of Wicker Park, plus specialty cocktails, wine and a sizable whiskey list. While it’s not technically a restaurant, The Up Room does serve bar snacks (a couple of cheese boards is an ideal dinner, anyway). If you’re not feeling a swanky rooftop, The Robey’s new Cabana Club just re-launched this summer. The semi-private day club has free entry Monday through Thursday and is $20 for adults on weekends ($5 for kids), which includes pool privileges and 360-degree views.
2018 W North Ave, Chicago, IL 60647
Miru
“Miru” is the Japanese word for “view,” which couldn’t be more accurate for this rooftop restaurant at the St. Regis Chicago, where you can dine while overlooking the trifecta of the Chicago River, Navy Pier and Lake Michigan. The restaurant celebrates the flavors and cuisines of Japan, with shareable dishes, sushi, cocktails and much more. The brunch menu is worth setting a weekend alarm clock for, with a Japanese-inspired breakfast spread, plus dishes like fried rice, breakfast bao and more. Bonus tip: make your reservation for a Wednesday or Saturday evening to get a birds eye view of the Navy Pier summer fireworks display.
The St Regis Hotel, 401 E Wacker Dr, Chicago, IL 60601
Sifr
Sifr’s bright, beautiful rooftop is the ideal spot to enjoy the restaurant’s creative Middle Eastern cuisine, which is mostly cooked over a charcoal and wood-fired hearth. The family-style menu includes massive mezze platters, dips, grilled seafood, shareable mains and varieties of Turkish pide. It’s also located in River North, making it the perfect spot to bring your favorite coworkers for a post-office happy hour. And be sure to come thirsty — the menu features a wide range of wines, with a bunch of sparkling, rosé and orange wines that are perfect for a summery moment.
660 N Orleans St, Chicago, IL 60654
Whiskey Business
If you’re feeling nostalgic for the ’80s and ’90s, Whiskey Business has you covered. The themed restaurant has delightful pop culture references throughout the space and throwback dishes on the menu — think grilled cheese, deep fried Uncrustables and Capri Sun. The massive 3,000-square-foot rooftop is a hub for events all throughout the summer, like movies under the stars, karaoke nights, yoga and much more.
1367 N Milwaukee Ave, Chicago, IL 60622
Upstairs at the Gwen
Upstairs at the Gwen combines vintage glamor with contemporary elegance in an Art Deco-inspired space. The rooftop, which was recently recognized by Conde Nast Traveler’s Readers Choice Awards, offers cocktails, a large menu of American food and an unbeatable view of the city — plus a happy hour with $11 apps and cocktails. But don’t miss the winter months at The Gwen when the space switches to warm drinks, fire pits and even curling on the terrace.
521 N Rush St, Chicago, IL 60611
Kindling Downtown Cookout and Cocktail Terrace
Kindling Downtown Cookout just opened the Cocktail Terrace, a massive 3,400-square-foot space at Willis Tower, making it one of the largest terraces on the Loop. It’s is an extension of the main restaurant, with the same live fire show kitchen, wood-fired plates and large cocktail menu. Don’t miss the raw bar with seafood that’s flown in daily, the fresh pasta and rotisserie chicken.
203 S Franklin St, Chicago, IL 60606
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