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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.
 

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for some reason i dislike nyc's skyline it just has too many buildings,i never thought i could say that but its the truth
 
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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.
 

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I would say Chicago, NY might more skyscrapers but Chicago Skylines looks much better and impressive.

Hong Kong is the Best in the World and then Chicago.

Chicago
NY
LA
SF
Seattle

and then the rest
 

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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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NY is the clear winner by far. It's core is unbelievably dense and just plain awe inspiring. There is no other city in NA that even comes close to the breadth of architecture and sheer enormity of NY.
 
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