The best rooftop bars in Chicago

Perhaps you’re looking for the perfect first-date location, or maybe just a nice place to make the most of a nice day, have a drink and take in a beautiful view. Regardless, there’s nowhere quite as romantic and enchanting as a rooftop bar with sprawling city views, especially if the dramatic skyline belongs to Chicago. Luckily, there are plenty of rooftop bars to choose from in the city, from local, hidden gems to luxurious cocktail lounges. Here are seven of the best rooftop bars in Chicago.

Drumbar | Photo courtesy of Raffaella Hotel

Drumbar (18th floor bar of the Raffaello Hotel) 

Address: 201 E. Delaware Pl, Chicago, IL 60611

This impressive cocktail bar is located in the Gold Coast neighborhood, atop the Raffaello Hotel. Inside this trendy speakeasy-style establishment you’ll find intimate, mid-century inspired Mad Men style decor. Outdoors you’ll find a beautiful terrace with views over the river.

Dec Rooftop Lounge and Bar | Photo courtesy of Ritz -Carlton Hotel

The Dec Rooftop Lounge and Bar (Ritz-Carlton Hotel) 

Address: 160 E Pearson St, Chicago, IL 60611

With casual elegance and French inspired cuisine, this is the perfect spot to sip on a drink and watch the world go by. With the stylish elegance and sophistication you’d come to expect from a Ritz-Carlton Hotel property,this place is truly something special, and one of the best rooftops in the city.

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Photo courtesy of Fountainhead

Fountainhead Rooftop Bar 

Address: 1970 W. Montrose Ave, Chicago, IL 60613

This low-key rooftop bar on the city’s North Side serves up a big selection of beer and organic pub food (to soak up the drinks). Lesser-known among tourists, this bar is a great choice for those looking for something a little more local with a fun, friendly, neighborhood vibe.

Photo courtesy of Twisted Spoke

The Twisted Spoke

Address: 501 N. Ogden Ave, Chicago, IL 60642

For those looking to escape the pricey downtown tourist traps, the motorcycle-themed Twisted Spoke is just a 15-minute drive from Michigan Avenue. Look for the motorcycle-driving skeleton beckoning from the rooftop of this quirky and comforting spot. Then settle in with a craft beer—there are almost too many to choose from—and one of their famous burgers. The friendly, home-style vibe will have you coming back again and again.

Terrace at the Trump | Photo courtesy of the Trump

The Terrace at Trump (Trump Tower) 

Address: 401 N. Wabash Ave, Chicago, IL 60611

For glitz, glamor and all things luxury, spend an evening sipping cocktails at Trump Tower‘s The Terrace. Of course, the majority of Trump’s buildings are known for their luxurious appeal, and this one is no different. Although the drinks may be expensive, the views are unrivalled here, so make sure you have your camera on-hand to take some photos.

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Vertigo Sky Lounge | Photo courtesy of Dana Hotel

The Vertigo Sky Lounge (26th floor of the Dana Hotel & Spa)

Address: 2 W. Erie St, Chicago, IL 60654

This lounge on the 26th floor of the Dana Hotel & Spa, boasts some of the best views in the city, with sweeping vistas over the dramatic Chicago skyline. The rooftop patio is year-round, although wrapping up warm in the winter months is recommended! The connecting lounge also has a nightly DJ, for any party-people reading.

Roof on the Wit | Photo courtesy of the Wit Hotel

Roof on The Wit (27th floor of theWit Hotel) 

Address: 201 N. State St, Chicago, IL 60601

Known as Chicago’s coziest rooftop, this bar is known for an intimate atmosphere and a warm welcome. In addition to its extensivedrink menu (with some delicious cocktail creations!), the bar also serves up some of the best seafood in town.

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Tagged: Midwest