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I'd probably pick LA. NYC is just too built up and crowded.
Chicago and LA are a bit more spread out.
As far as the women thing goes, NYC area native women tend to be either aggressive/masculine or finicky Jewish-American Princesses. (Not being racist).
Since you listed cost of living as one of the parameters, Chicago hands down. Also has a lot of young people and a decent public transit system. Only downside is the weather and crime.
I would say the women are generally pretty hot in LA but many genuinely think their s*** don't stink. Kind of the same in NYC but there are more women to men ratio there.
Still gotta go with LA. It's just a better quality of life over NYC and much better weather. I personally don't like the crowds either. And you can have a savings account in LA whereas I don't think it's possible in New York.
Public transit is getting better as well. Nowhere near the levels of NYC and Chicago, but by next year you can take the Metro from Santa Monica to DTLA. That's a milestone -- hasn't been possible to do that in over 60 years. But if you are highly dependent on PT and don't like driving, that's a deal breaker for LA. I personally like driving so it's fine by me.
With regards to dating chicks: You got the awful sex in the city mentality in NYC, the stuck up modeling mentality in LA, and the chubby beer drinking chicks in Chicago. Can't win
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