First things first, it's rather alarming how many people have weighed in here who have said "I haven't ever been to Chicago, but..." Go to Chicago. Maybe then your opinion will mean something. Also, get out and visit the US. If you haven't been to Chicago, where else haven't you been? It's a big country, so get out there and see it.
Second, the question of NYC vs Chicago is going to boil down to different strokes for different folks. My wife and I were looking at NYC a year ago because I was switching firms and she was beginning residency. My brother and sister both live in NYC and most of my friends from college are out there, but ultimately we decided to stay in Chicago.
I guess I will go thru some of our pro/cons in deciding:
Chicago pros:
-Costs of living are low. My place is way nicer than my brothers and costs way less and I live in the most expensive part of Chicago and he lives in Brooklyn.
-Having a car is not a pain
-Lots of good jobs
-Good grad school options in Northwestern and UChicago
-Good professional sports, venues are easy to get to
-Hot dogs
-Italian beef
-Mexican food
-People are nice
-Nice suburbs if you want to make the move
-Very nice commuter rail system
-Big airports both accessible via public transit
-Blues
-Not too difficult to become a big fish in what is quite a big pond
Chicago cons:
-Locals have annoying accents
-Having a car is easy therefore traffic is bad
-Weather is bad
-Corruption
-Midwestern rubes
-Sales tax is very high
-Bad Chinese food
New York pros:
-The best jobs are here
-There is just more of everything
-Better shopping, more high end places to get the finest things
-Better pizza
-Better Chinese
-Lots of very smart people from the best schools
-Subway can get you anywhere
-Columbia and NYU
-Beautiful women and lots of them
-Big airports
-More old buildings
-A 24 hour city
New York cons:
-Everyone's success is thrown in your face and it becomes a lot of "keeping up with the Joneses"
-Locals have annoying accents
-People are totally inconsiderate (one of my biggest pet peeves of NYC and something that definitely had a strong influence on my not moving there. there are just so many people there who don't understand propriety, decorum, rules, politeness, etc., or worse, people who know the rules and just don't think they apply to them).
-Island nature of NYC makes it very hard to get out of the city quickly, cheaply, easily
-Smells
-Is loud
-Weather almost as bad as Chicago
-East coast snobs
-Extremely competitive
-Grocery shopping is a huge inconvenience
-Income taxes
