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With a long and storied architectural history, Chicago has one of the most jaw-dropping skylines of any city ever. Want proof? Check out one of the ten spots below and say goodbye to your mind, because it’s about to blow.

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Chicago Athletic Association

Every inch of this 11-story building is a meticulous tribute to old-school, American design. Cindy’s Rooftop Bar, the “crown jewel” of the Chicago Athletic Association, offers views of Millenium Park that make you fall in love with the city all over again.

12 S. Michigan Ave.; 312-792-3502 or

J. Parker

J. Parker

Perched atop the Hotel Lincoln, J. Parker offers the sort of view that pairs perfectly with a cocktail. Our rec? Try the Moonage Daydream--a delicious concoction made with coconut and orange-flower water. There’s no better way to toast the last days of summer.

1816 N. Clark St., 13th fl.; 312-254-3737 or


Lakefront Trail

Get active as you feast your eyes on the magnificence of our fair city. The trail runs all along Chicago’s Lake Michigan coast, which means you’ll never run out of new vantage points to enjoy.

4300 N. Lincoln Ave.; 312-742-7529 or


The Signature Lounge at the 96th

Come on, how could we not mention the John Hancock on this list? At 96 stories high, The Signature Lounge gives guests an unparalleled view of the city--you can practically see straight to Michigan on a clear day. 

875 N. Michigan Ave.; 312-787-9596 or



Frequented by the Obamas, Spiagga is a certified Chicago institution, serving up delicious food alongside an equally delicious view of the Magnificent Mile. Not feeling so fancy? Try Café Spiagga. You get all the sights for a fraction of the price.

980 N. Michigan Ave.; 312-280-2750 or


Grant Park

If Spiagga is at one end of the spectrum, Grant Park is at the other--totally free! Swing by on a sunny afternoon for a gorgeous, panoramic look at the buildings that line the lakeshore. It’s the best deal in town.

337 E. Randolph St.; 312-742-3918 or

Drum Bar

Drum Bar

Sip on some upscale whiskey as you take in the spectacular Chicago skyline. With 18 inventive and unexpected cocktails on the menu, we hereby proclaim this the perfect date night spot. 

201 E. Delaware Pl.; 312-933-4805 or


Tavern at the Park

We love Chicago, but let’s not kid ourselves: Sometimes the weather is, um, less than ideal? That’s where Tavern at the Park comes in. With indoor and outdoor views of South Michigan Avenue and Millennium Park, you’ve got year-round eye candy waiting for you.

130 E. Randolph St.; 312-552-007 or

North Pond/Facebook

North Pond

Located in the heart of Lincoln Park (the actual park), this might just be the most romantic spot in the whole city. Whether you’re splitting the tasting menu with your main squeeze or ordering à la carte with your besties, North Pond gives you both town and country in one look.

2610 N. Cannon Dr.; 773-477-5845 or



As if BYOB concerts in the park weren’t a big enough draw, J. Pritzker Pavilion also boasts some of the most OMG views in the city. Throw out your blanket, lie down and look up. It’s the three easiest steps to a perfect summer evening.

55 N. Michigan Ave.; 312-742-1168 or

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