Believe it or not, I'm going to go with Chicago for now. Once the Freedom Tower is completed I will probably give it back to New York but as it stands it's Chicago that will have the more modern and taller skyline. I guess I'm just not much of a fan of early 1900's style architecture although I know New York has plenty from all eras. In terms of the dominant towers though, Chicago takes this one to me.
i think 'best' can mean a lot of things. New York is certainly the biggest, Chicago is certainly the tallest, but best is more just people's personal opinions. A lot of people prefer an extremely dense core, which neither New York or Chicago have.
For now i'd say New York, but only slightly ahead of Chicago. Give Toronto 20 years and it might be able to give them a run for thier money. I do think that Vancouver has a nice skyline, but nothing compared to the behemoths of the east.
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