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Unexpected Skyline Views

There's more than one way to see the city.

Whether you’re just visiting Chicago or you’ve called the city home for years, catching an unexpected glimpse of the skyline never fails to stir up some excitement. You don’t need to be out on the lake to get a good view either –plenty of spots on the North, South and West sides offer striking views of Chicago’s skyline.

The Penthouse Hyde Park

5107 S. Blackstone Ave.

Whether you’re inside or outside at The Penthouse, you’ll be treated to a breathtaking look at the city, thanks to the ballroom’s towering 20’ arched windows and the accompanying rooftop terrace. Not to be outdone by the view, The Penthouse’s interior masterfully blends contemporary design with 1920s art deco flair that is original to the building.

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Nichols Tower at Homan Square

906 S. Homan Ave.

We all know that before it was the Willis Tower it was the Sears Tower, but did you know there was another Sears Tower long before Chicago’s iconic skyscraper came to be? The Neo-Classical Nichols Tower is all that remains of the once-sprawling Sears, Roebuck & Co. complex. Ever since its restoration in 2016, visitors have been flocking to the top of the tower to take in its sweeping Westside view of Downtown.

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Sable Hotel

900 E. Grand Ave.

Perhaps the most unique view of the skyline on this list, the new Sable Hotel at Navy Pier allows you to take in the city from 3,000 feet out on Lake Michigan. Each of the hotel’s 223 guest rooms feature floor-to-ceiling windows, so you’re guaranteed a good look at Chicago’s downtown when you visit this site.

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CAC Members Only

360 CHICAGO Observation Deck

875 N. Michigan Ave., 94th Floor

CAC MEMBER EXCLUSIVE SITE: Tower over the skyline at this observation deck, located on the 94th floor of 875 N. Michigan Ave. If you’ve seen enough of Chicago at this point, train your gaze slightly farther out; on a clear day, you can see three other states from the deck! This OHC site is only available for CAC members – join today to guarantee your spot.

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Sky-Line Club

307 N. Michigan Ave.

This one might be a bit on-the-nose, but with a name like “The Sky-Line Club,” how could we not include it? After taking in the skyline from various vantage points throughout OHC weekend, cap things off by putting yourself in the middle of it all at this members-only facility atop the Old Republic Building.

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Now you know OHC staffers’ tips and tricks for staking out the best view of the city. But do you ever wonder how Chicago’s iconic skyline came to be? Much of downtown’s built environment can be directly or indirectly credited to the Great Chicago Fire, which leveled the city center 150 years ago. Trace the path of the infamous blaze and learn about its lasting impact on the city’s architecture with the Great Chicago Fire self-guided walking tour. You can find this trail, along with many other trails, on the OHC app.

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