Known for its world-renowned architecture, Chicago has more than its fair share of stellar skyscrapers. From the Willis Tower and John Hancock to more modern examples like The St. Regis and NEMA Chicago, famous architects keep coming back to put their mark on our skyline. We have dozens of skyscrapers making up our world-class skyline, but there can only be one that’s the best.

In the spirit of March Madness, it’s time to figure out exactly which of those is our best skyscraper. We have narrowed it down to the 16 tallest projects and can’t wait to see who we crown as the winner! 

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(5) John Hancock Center

John Hancock CenterSOM


875 N. Michigan

Height: 1,128 feet

Floors: 100

Constructed: 1965-1969

Architect: Skidmore Owings Merrill (SOM)

Developer: John Hancock Mutual Life Insurance Company

John Hancock CenterSOM

Now known at 875 North Michigan Ave (another name changer), the building was the world’s first mixed-use tower, containing office space on the lower floors, residential units on the upper floors, and an observation deck and restaurant at the top. The skyscraper’s tapered shape was chosen to match the different floor space requirements of the different uses. The facade uses an exterior diagonal tube structural system, sometimes referred to as a diagrid, to support the building.

(12) Water Tower Place

Water Tower PlaceCoStar


845 N. Michigan

Height: 859 feet

Floors: 74

Constructed: 1972-1976

Architect: Loebl Schlossman Hackl

Developer: Urban Retail Properties

Water Tower PlaceCTBUH

Located just across the street from its competitor in this round, Water Tower Place is another mixed-use skyscraper completed in the mid-1970s. Standing as the tallest reinforced concrete building in the world when completed, it contains a 435-room Ritz-Carlton hotel, 360 condominiums, and office space all perched atop a large vertical mall in the podium. Oprah Winfrey owned four condominium units before selling them in 2015 and 2016. The building and its mall have suffered during COVID which included the departure of Macy’s in 2021.

Cast your vote below!

UPDATE! The poll has closed. The John Hancock Center will move on to the Elite Eight!