You can find anything on the web, including a ranking of the top 100 cities by the visual impact of their skylines. The top four cities are Hong Kong, New York, Seoul, and Chicago.
Speaking of the Windy City, I miss Fluky's, the great restaurants, the neighborhoods, family and old friends.
Other great cities on Jeffrey's scale (must have good food, neighborhoods, a bit of culture, and fun) include: Boston and San Francisco. I think New York, Atlanta, and possibly Denver might make the list too, but I don't know enough about them from personal experience.