You can find Homestead on the Roof at 1924 W Chicago Ave. Then, thereâs the winding Chicago River with its buzzing waterfront and glittering Lake Michigan. While the English-style pub is dark, cozy, and perfect for a frigid late fall or winter Chicago day, itâs the open-air rooftop where you want to snag a table in warmer months. This stylish and modern eatery based in Hyde Park is perfect for a low-key evening of excellent food and live music. For dessert, we suggest trying their “The Celebration” ($5/person), a slew of coffee shots served with birthday cake macaroons. I used to work in the Tribune building and they have a great balcony, as the previous commenter mentioned. The best rooftop restaurants offer both great food and city views, whether you're gazing at views of the Chicago Loop or glimpses at neighborhood architecture. Then we suggest heading over to the Prairie Terrace at the Ace Hotel. Here you’ll find a wide seasonal array of handcrafted cocktails, shareable plates and local craft beers as well as the usual pop-ups by local businesses. Rooftops with food, drinks, and activities as well as igloos and covid-friendly fine dining. Lounge around in the sun with a drink in your hand at one of the best rooftop bars in Chicago. True to its name, the views at VU are epic from 22 stories above street level. We already have this email. You can find AIRE at the Hyatt Hotel at 100 W Monroe St. With its glass-vaulted ceiling, this rooftop perched upon Chicago Athletic Association Hotel is an excellent choice come rain or come shine. Set in the heart of downtown Chicago, Upstairs at the Gwen is a stylish, open-air rooftop bar that features luxurious and trendy decor. Hit up this sweet Wicker Park rooftop for weekend brunch service, when you can enjoy tableside Aperol spritz service until you need to reapply your sunscreen. On particularly beautiful summer days, arrive early and be prepared to wait for a seat to open. Wrigley Rooftops is the trusted authority for fans looking to book group and individual rooftop tickets to Cubs games and other events at Wrigley Field. There's a Jewel on Chicago just west of Damen with rooftop parking and the views of downtown are incredible from there. As one of the best rooftops in the Loop, Cindyâs cocktails are balanced and aesthetically pleasing, to match the view. Their Chicago Mule ($11) with grapefruit and rose-infused vodka–a totally refreshing twist on the classic. By Adam Lukach. Their pasta team starts hand-rolling their dough at 5 am every morning for you to enjoy some delicious pasta dishes like their “Cavatelli Bolognese” ($16) that come served with a delicious parmesan fondue (). You can find the Prairie Terrace at 311 N Morgan St. But if you’re looking for a bit of (safe) partying, you’ll find that Joy District’s rooftop offers quite the lively scene after 5pm. At The Rooftop Bar at Nobu Hotel features you’ll be able to enjoy Nobu’s take on Japanese-Peruvian fusion cuisine in the shape of a wide range of small dishes such as nori tacos ($15/pc) with caviar and avocado, wagyu dumplings ($26) with smoked jalapeño miso that are perfect for sharing. If the sun is shining, wander outside to take in skyline views and enjoy a meal on the breathtaking terrace. Their 3,000-foot rooftop is awesome for a relaxed and laid-back time with friends while sipping on some killer drinks, whether you choose to chill out at their “Rooftop Beach Club” during the day or vibe with their dazzling new laser show “Neon Reef Nights” during your weekend nights! Downtown Chicago cocktails are balanced and aesthetically pleasing, to match the view Sculpin IPA buffalo wings and pork... 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