I grew up in the sticks of Connecticut. No public transportation in a town of 2,000 people. We would occasionallly take trips into Boston and I always loved it. There is something I find comforting in a crowd, in the hustle and bustle. It doesn't hurt that everyone in Chicago is so damn nice. People meet your gaze, return a smile, say hello. In that way it even beats out Boston.
The one thing I haven't mentioned yet is the money. In Chicago, probably like in any major city, there is a whole other realm of money above and beyond anything seen in Raleigh. A surreal moment is driving down Michigan Avenue, and there, written in the same kind of marker you see on the windshields of used cars for sale, is a sign scrawled across a store front window:
"Condos $1.5M and up."