The Year-Round Guide to Chicago's Best Rooftops
The Year-Round Guide to Chicago's Best Rooftops

The Year-Round Guide to Chicago's Best Rooftops

12 Places To Take In The Chicago Skyline All Year Long


From skyline hotel havens to tailgating terraces, Chicago has plenty of places to experience rooftop bliss year-round. Whether you’re looking for sprawling views, refreshing mocktails or a cozy fireplace with your rooftop, this list has you covered. 

Cindy’s 

 
 
 
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Located in the Chicago Athletic Association Hotel, Cindy’s is one of the city's best rooftop restaurants. With unparalleled views overlooking Millennium Park and the lake, Cindy’s makes for a perfectly relaxing rooftop experience. Pro tip: Indulge in their mocktail menu!

Where: 12 S Michigan Ave, Chicago, IL 60603 

Offshore

 
 
 
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Have your cocktails and eat oysters, too! Located at Navy Pier, Offshore lives up to its name with fresh cocktails, seafood and vibes. Did we mention it's the world's largest rooftop bar? From fire pits to live music, they have it all. 

Happy Hour: Daily, 4 pm - 7 pm for Chicagoland Residents 
Where:1000 E Grand Ave, Chicago, IL 60611 

Kennedy Rooftop 

 
 
 
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If 7,500 square feet of unobstructed views overlooking Chicago sounds like a good time, keep reading. Not only is Kennedy Rooftop spacious and comfy, but their cocktail menu also has some unique elixirs-- that pay homage to past presidents--you’ve ever tasted.  Visiting this winter? Igloos are awaiting you!

Where: 1551 W North Ave, Chicago, IL 60622 

 

Utopian Tailgate

 
 
 
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As its name suggests, Utopian Tailgate is a tailgating paradise. Think tableside coolers of beer, stadium seating and even cornhole. No off seasons here--this whimsical, lush space is open all-year around! 

Happy Hour: Monday - Thursday, 4 pm - 7 pm 
Where: 1608 N Wells St, Chicago, IL 60610 

 

The Up Room

 
 
 
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Located in the heart Wicker Park and inside of boutique hotel, The Robey, The Up Room is a city-dweller's dream. There’s a rooftop pool, picturesque views, and food for every palette here.   

Where: 2018 W North Ave, Chicago, IL 60647

 

Z Bar 

 
 
 
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Looking to jazz things up tonight? Z Bar is a swanky rooftop with sweeping vibes of the city. Their menu is inspired by the world's culinary riches, which is apparent with tapas like burrata with a pistachio pest and cocktails like the Manhattan Royale--a drink served in a crystal and with 24k gold. 

Where: 108 E Superior St, Chicago, IL 60611

IO Godfrey Rooftop Lounge

 

Credit: IO Godfrey Rooftop Lounge

Once you step foot into this gorgeous, open-air rooftop lounge, you may not want to leave. IO Godfrey is open all year, thanks to its retractable glass roof. On offer: sprawling views of the Chicago skyline, an impressive drinks menu, and some top-notch wagyu beef sliders. 

Happy Hour: Monday - Friday, 2 pm - 5 pm
Where: 127 W Huron St, Chicago, IL 60654

Boleo 

 
 
 
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Teleport to Argentina at Boleo. A 15th-floor rooftop that practically doubles as a tropical island. The music is flowing, and the Peruvian-inspired plates will keep you coming back.  

When: Wednesday - Friday, 4:30 pm - 7 pm

Where: 122 W Monroe St, Chicago, IL 60603

The Rooftop at Nobu Hotel 

 
 
 
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A swanky rooftop perched on the 11th of the Nobu Hotel. The brand's iconic flair is apparent here: candle light, cozy furniture, and a stellar menu. Best part? The views overlooking Chicago.  

Where: 155 N Peoria St 11th Floot, Chicago, IL 60607

 

Lonesome Rose 

 
 
 
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Located in Logan Square, Lonesome Rose brings a bit of Mexico to Chicago. Inspired by the street food of many Mexican cities, you’ll find everything from the classics (like chile con queso) to the experimental (like fried chicken tacos). And of course, the views are Insta-worthy. 

When: Monday - Friday, 3 pm - 6 pm
Where: 2101 N California Ave, Chicago, IL 60647

 

Upstairs At The Gwen

 
 
 
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If you visit Upstairs at The Gwen in the warmer months, it’ll be lovely. But wintertime here is the real star. There are cabins to cozy up in, faux furs, and alpine-inspired bites--careful, you might mistake it for Switzerland.  

Happy Hour: Monday - Thursday, 4 pm - 5:30 pm

Where: 521 N Rush St 5th Floor, Chicago, IL 60611 

 

Devereaux

 
 
 
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Located on the 18th floor of the Viceroy Chicago hotel, Deveraux is just as classy as its moniker. Lush greenery surrounds the rooftop pool. And classic cocktails are done right with a twist! Pro tip: The Beet Tartare is a crowd-pleaser. 

Happy Hour: Monday - Friday, 5:30 PM - 7 PM
Where: 1112 N State St Chicago, Illinois 60610

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