Chicago has everything
Fresh water, a big downtown, unique and diverse neighborhoods, nightlife, colleges, change of seasons, quiet areas and busy areas. And, I'm not sure whether it's a good thing that Chicago doesn't get the attention that cities like L.A. and New York get. This "undergroundness" of the city is part of it's character, and Chicagoans are some of the most down to earth people around. This, also detracts from the nonstop eccentricity of the two aforementioned cities that is part of their character as well. New York is a great place to visit, but not to live. Too expensive also. Unless you're a lawyer or a third generation Yale grad you can't afford to live in Manhattan like you used to. But i digress, choose Chicago you won't regret it.