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Location: Concrete jungle where dreams are made of.
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NYC beats Chicago's skyline by far. I think the longer the skyline, the better. I laughed at this thread in Florida's forum where they asked which city in FL has the best skyline. Those aren't skylines...lol. I laughed even harder when people said that like Talahassee has a skyline.
The original question was, what makes NYC's skyline great? And the answer is...the sheer size and diversity of the buildings. I don't say that Chicago has an inferior skyline, but, hey, let's face it: Chicago is only half the size of New York!
Actually, looking at the photos, Chicago's skyline reminds me somewhat of Brooklyn's. (Yes, Brooklyn has a skyline. But you don't notice it next to what's on the island of Manhattan).
The best view of the skyline is Midtown as seen from Long Island City. "What makes is so great" is that from certain angles you can't see sky between the buildings; it appears to be a 700+ foot wall glass and steel. Downtown as seen from the Staten Island Ferry is perhaps more elegant (and certainly more romantic), but Midtown from the East River displays the awesome immensity of the city like no other vantage point. The only other city that can compare is Hong Kong.
And when you're flying home, there's NOTHING like looking out the window and seeing the statue of liberty. That's something Chicago will never have.
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