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! 


(2) Trump International Hotel and Tower

Trump International Hotel and TowerThe Trump Organization


401 N. Wabash Ave

Height: 1,389 feet

Constructed: 2005-2009

Floors: 98

Architect: Skidmore, Owings, Merrill (SOM)

Developer: The Trump Organization

Trump International Hotel and TowerThe Trump Organization

Formerly the site of the Chicago Sun-Times, our former President developed the building which holds 339 hotel suites, 486 condos, and a rooftop restaurant with great views of the city. Designed by SOM, the project was originally planned to be the new world’s tallest building, but was stunted by a few hundred feet in the aftermath of 9/11. The setbacks of the metal and glass tower respond to the heights of nearby landmarks, matching the heights of the Wrigley Building, Marina City, and the IBM Building.


(15) Park Tower

Park TowerLucien LaGrange Studio



800 N. Michigan Ave

Height: 844 feet

Constructed: 1998-2000

Floors: 67

Architect: Lucien LaGrange & Associates

Developer: Hyatt Development

Park TowerCTBUH

Gracing the Mag Mile skyline, Park Tower is one of the tallest concrete framed structures in the world, also holding the title of first building in the United States to use a tuned mass damper. Weighing 300 tons, the tuned mass damper counteracts wind effects on the structure by providing inertia that stabilizes the building. With a mixed-use program, the bottom floors house 203 hotel rooms for the Park Hyatt hotel, with 117 condominiums on the upper floors. 


Cast your vote below!

UPDATE! The poll has closed. Trump Tower will move on to the elite Eight!