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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(3) St. Regis Chicago

St. Regis ChicagoTom Harris


375 E. Wacker

Height: 1,196 feet

Floors: 101

Constructed: 2016-2020

Architect: Studio Gang, bKL Architecture

Developer - Magellan Development Group LLC

St. Regis ChicagoStudio Gang

Now the city’s third-tallest building, the St. Regis Chicago holds 192 hotel rooms, 393 condominiums, restaurants, and shared amenity spaces. The design presents itself as three interconnected volumes that undulate as it rises, giving it a flowing appearance. The undulating form is made possible by the 12-story truncated pyramids called frustums, which are stacked and nested to create a building with eight corners instead of four. This form gives inhabitants daylight and fresh air from multiple orientations. 

(14) Chase Tower

Chase TowerCTBUH


21 S. Clark St

Height: 850 feet

Floors: 60

Constructed: 1966-1969

Architect: Perkins & Will and C.F. Murphy Associates

Developer: First National Bank of Chicago

Chase TowerPerkins & Will

Located in the heart of the Loop, Chase Tower opened in 1969 as the First National Bank of Chicago. With its distinct curving shape, the building became the headquarters for Bank One Corporation in 1998 before becoming Chase Tower in 2005 after the merger between Bank One and Chase. Now the 14th tallest in Chicago, the tower was the world’s tallest skyscraper outside of New York and the tallest bank structure at the time of its completion. At the base, the site is completed by a deep sunken plaza with a jet fountain and Marc Chagall’s ceramic wall mural dubbed Four Seasons.


Cast your vote below!

UPDATE! The poll has closed. St. Regis Chicago will move on to the elite Eight!