QuietC,

I grew up in Chicago, am here for the summer, but spend most of my time in NYC now. I went to Miami U. undergrad, so I understand the Ohio mindset (Get the hell out once I graduate). NYC and Chicago are both awesome places to live if you don't mind the weather (which is the same weather you pretty much grew up with in Ohio). But, both are in the top 5 of Forbes most overpriced cities. If I had to choose one I'd do so asking myself certain questions:

1) What is the specific industry I want to work in?
2) Do I want to buy a car and pay for all a car costs?
3) Do I really want to live in either climate, shouldn't I just move to Cali where it's always 70 degrees?
4) Where do I have more people I know?
5) How much culture do I want available at my fingertips: a) a lot, or b) endless amounts?

PM me if you ever want to have a phone conversation about this, like I said, I grew up in Chicago, still spend my summers here (I'm a graduate student), but live in NYC otherwise.

I love both, the questions above are the key.