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In my opinion I'd have to say Chicago. Chicago's skyline is unique and presents so many different angles, very long and linear from one view yet very dense and clustered from another. The variations in height, color and architecture of the different skyscrapers, the contrast along Lake Michigan's shoreline, Navy Pier, the way the Chicago River winds and bends through the middle of the city, it is impossible not to get an excellent view or panorama from Chicago.
I'd have to go with Chicago with Seattle as a runner up. NYC has tons of amazing architecture, but it's laid out in this garbage-y pattern so you really can't appreciate it as much as you would if there was some space. I love SF, but I don't see it as being better than Chicago in terms of photographs.
I would say Portland or Seattle, especially when it is sunny out.
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Seattle
