Chicago is New York City taken in moderation.
New York is Chicago taken to excess.
The midwest is a place that identifies with moderation. Midwesterners are proud of their great metropolis. Chicago is quite the wonder! But then, they will admit to being uneasy about that big big city.
New York sees itself on the level of London, Paris, or Tokyo. New York is the cultural axis around which a great nation revolves.
Chicago sees itself rising from the plains. Chicago is the great version of Milwaukee, or Detroit. Chicago gave birth to the skyscraper and the Loop has a certain antiquarian flair, with the screeching L line at the center.
Chicago spreads out on the plain . . . tall buildings in the center, and miles upon miles upon miles of neighborhoods and factories, which give way to suburbs and corporate headquarters, which give way to the farms and small midwestern towns that are every year sucked into the growing conurbation.
New York? Ocean on one side, mountains on the other, and the sprawl runs directly into Philadelphia and Boston.
I think Chicago feels a lot like a small Berlin, fewer trains and monuments, less tragic history. Greek gyros instead of Turkish doners. Germany is the heart of Europe from which many of the white midwestern people came. As Chicago is the great underrated city of America, so is Berlin the great underrated city of Europe. I think Chicago will in time grow into a Berlin, and just as people overlook Berlin for Paris, people will still be overlooking Chicago for New York.
But at least its not L.A.