Chicago- I love Chicago. I lived an hour away for six years and while my friends would beg our parents to take us to Six Flags, Id beg to go to the city. Chicago was my home, and second to Hawaii, its my favorite place on Earth. I loved Lincoln Park, Brooklyn Zoo, sitting in Comiskey watching the game with the projects peeking over the walls (yes, for some odd reason, I liked the projects), going to the top of the Sears Tower and everything. I also liked the annual airshow where wed go and swim in the lake while the Blue Angels flew overhead.
New York- Ive been to New York for a day (post Sept 11, never saw the WTC) in my life and I loved it. You cant see everything in a day but we saw a lot of it. Theres Time Square (which, like someone said earlier, is one of the coolest places there is) where you have the naked cowboy (only in NY ) and excellent breakdancers. Theres the Empire State Building and Greenwich Village. And some people say New Yorkers are mean. Not at all. There were several locals we met that talked to us just about anything for no real reason other than to be nice. They were very welcoming people who were hard to not like.
My consensus is the same as the others. Chicago is home, New York is the party...