What happened to New York? I has the most famous, most photographed and best-loved (or so I thought) skyline in world, and in skyscraper statistics it beats the hell out of any other city. But guess what... in my Favorite Skyline Poll (http://www.library.tudelft.nl/~egram/skypoll.htm) it is now second after Chicago. Withpout denying the quality of Chicago's skyline, I think something is not right here.
The reason why Chicago's skyline is better, in my opinion, is that you can see more of it from more angles. New York's density makes the skyline there difficult to appreciate from street level. Ans plus, every skyline is painted on a canvas and Lake Michigan is a much better canvas than the Hudson River.
Ehi guys, don't joke ! It's impossible to say from an aesthetic point of view that Chicago skyline is better than NYC, for the number of scrapers, the diversity of age/years, style... and the diversity of the point of view from where you can see the city: for example Chicago has only a good view from the lake, but NYC has good views from Hudson, Liberty Island, East River. And has not just a group of scrapers but two very different: midtown and downtown, so the skyline is really different if you consider different part of the city.
I really wouldn't trust a poll a chicago geek could be up all night hitting enter and hitting the reload button. Fact is New York has more than double the amount of skyscrapers (above 500 feet) and more diversity. It is by far the pick by many, ofcourse not all.
I'm a big architecture buff and have studied the history of the skyscraper. Historically, Chicago has been not only an intregal force in the rise of the modern high rise but for you New York numskulls has also been the city that has developed the skyscraper. For many years Chicago has been regarded to have the best examples of city architecture according to the American Institute of Architects. Even more so than New York. In response to the comment that New York has many great angles from which to view the skyline, Chicago also has many great views from which to view and photograph it's own skyline. Thanks for pointing out that a city has many angles from which to view it or photograph it from. Chicago's downtown doesn't seem to be cluttered as New York's. So maybe a Chicago geek may have pushed the enter button many times over, but it goes to show you how passionate we are about Chicago's skyline over New York's.