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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(7) Two Prudential Plaza

Two Prudential PlazaCTBUH


180 N. Stetson

Height: 995 feet

Floors: 64

Constructed: 1988-1990

Architect: Loebl Schlossman and Hackl

Developer: Prudential

Two Prudential PlazaCTBUH

Completed in 1990, Two Prudential Plaza was the world’s tallest reinforced concrete building. The design consists of a series of stacked chevron setbacks that culminate in a pyramidal peak that is rotated 45 degrees. The tower is connected to its sister tower One Prudential Plaza at its base. 

(10) NEMA Chicago

NEMA ChicagoRafael Vinoly Architects


1210 S. Indiana

Height: 893 feet

Floors: 76

Constructed: 2017-2019

Architect: Rafael Vinoly Architects

Developer: Crescent Heights

NEMA ChicagoRafael Vinoly Architects

As Chicago’s tallest rental residence, NEMA Chicago has been designed to resonate with the best of Chicago School architecture and complement the skyline of towers along Grant Park. Similar to the Willis Tower, the structure uses a bundled tube configuration of nine steel tubes with concrete walls extending to the perimeter for wind protection. Recently completed in 2019, the building has 800 apartments and 70,000 square feet of amenities. 

R.I.P. Rafael Vinoly 1944-2023


Cast your vote below!

UPDATE! The poll has closed. NEMA Chicago will move on to the Elite Eight!