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! 

Cross referencing between CTBUH and SkyscraperPage our lineup looks like this:

Chicago Skyscraper Tournament

With voting open today, we’re beginning with our first matchup:

Willis (Sears)

(1) Willis Tower


233 S. Wacker Drive

Height: 1,451 feet

Constructed: 1970-1974

Floors: 108

Architect: Skidmore, Owings, Merrill (SOM)

Developer: Sears Roebuck and Co

Willis (Sears) TowerSOM

Currently our tallest building, the Willis (we know it's really Sears) Tower, is an engineering marvel from SOM, using a bundled tube system of nine squares that allow the tower to achieve a 6.45:1 height-to-width ratio. Costing $160 million when completed, the construction used 76,000 tons of steel, 72,000 cubic yards of concrete, 17,500 tons of mechanical equipment. After years of ownership changes, Sears lost the naming rights to new tenants Willis Group Holdings who gained the naming rights in 2009. The building is currently owned by Blackstone Group, who bought the skyscraper for $1.3 billion in 2015.



One Bennett ParkRobert A.M. Stern Architects

(16) One Bennett Park


451 E. Grand Ave

Height: 837 feet

Constructed: 2016-2018

Floors: 67

Architect: Robert A.M. Stern Architects

Developer: Related Midwest

One Bennett ParkRelated Midwest

Coming in at 16th place, One Bennett Park is one of the most modern examples in our list, even though it may not look like it. Designed by Robert A.M. Stern, the slender tower rises clad in precast concrete and topped by an asymmetrical crown. The building is currently home to 280 rental apartments and 70 condominiums which feature a separate entry into the building. The tower meets the ground with a large park space that was designed by Michael Van Valkenburg Associates.


Vote below to decide our first matchup!

UPDATE! The poll has closed. The Willis (Sears) tower will move on to the elite Eight!