Best place to visit = NYC
Best place to live = Chicago IL. So so much to offer and is a much cleaner, friendlier city. The lake and the beach give it that little bit extra.
I'd say that Chicago is the best place to visit as well.
I love New York and never thought I'd love a city as much, but Chicago is that city. It's a wonderful place. Def. a more 'good looking' city than New York as it where
The down town areas and N Michigan, the parks, the lakeside and river, the beaches are positively sparkling - don't think I've seen a city that seems to have city workers constantly cleaning and tidying. And the sky line is second to NONE in the US.
But also, it has the diversity that New York has with interesting and more 'lived in' neighborhoods close by, such as Wicker Park, Bucktown, Pilsen etc etc.
Also, Chicago is a more sports mad city than New York, maybe cos it's more compact and all their teams play in Chicago. Whereas in NYC where 2 of the teams don't even play in the same state, and all but 2 are spread out.
I was in Chicago couple weeks ago, and I've never seen so many fans of one team (the Cubs), about a city, the place was just full of 'em, everywhere you turned - people in Cubs get-up. It was great.