For as long as there've been skyscrapers, Chicago and New York have been elbowing each other for dominance over the sky. Late in 2013, the Chicago Tribune's Blair Kamin did his best to downplay a controversial decision* by the Council on Tall Buildings and Urban Habitat that gave the upper hand to New York. One World Trade Center bested Willis Tower, the former Sears Tower, as the nation's tallest skyscraper.
Size is just one dimension to the contest (and for most of the 20th century, New York led this measure). On subjective design criteria, it's harder to judge who comes out on top. There is no council tasked with deciding between Chicago's 330 North Wabash, Marina City, and Aqua Tower, on the one hand, and New York's Woolworth Building, 432 Park Avenue, and New York by Gehry, on the other.