Chicago is windy as fuck and is shit town miserable in the winter.
New York is king of cities. I would never, ever move anywhere else. Case in point: Yesterday after work we went kayaking FOR FREE on the Hudson River. Then we walked for a bit nabbed some HELLS YEAH pizza for like 10 bucks and then went ti Bryant Park to watch Bride of Frankenstein on a giant ass movie screen and drank wine with a bunch of French ex-pats.
If I HAD to pick another city to move to it'd be Chicago, But New York lights my fire, man. I can't understand why anyone lives anywhere else. If you'd like to come for a visit, lemme know.
Also, NYC public transport is great. But also, uh, egalitarian. Expect to ride with Mrs. Upper East Side Moneybags on your right side and Mr. I Don't Bathe But You're Going to Hell Because I'm Crazy on your left. It is an experience.