The biggest difference is in the attitudes of the people about their city. I have never heard anyone from NYC say, "I hope this compares to whatever Chicago is doing!" But everything in Chicago is based upon how it can beat out, or look better than, NYC. Chicago has a massive inferiority complex that will only get worse as places like Houston and Phoenix grow bigger than them. NYC doesn't have to compare though. They know they are the best, and honestly, couldn't care more what happened in Chicago. There is nothing in Chi-town that cannot be found in far more quanity and quality in NYC. Chicago strives to be NYC, but the same can not be said that other way around.