Since Frank Sinatra sang that Chicago his kind of town, we felt that you also may find it too your liking. Chicago is the largest city of the entire Midwest. New York Done Right is a breezy nickname for the city that does not receive quite the mileage as some of its other more recognizable globally recognized nicknames. But it is a favorite of the locals that could get a visitor a free beer from a friendly bartender. Although it is among the most » Read more: Luxe City Guide: Chicago