I've lived in a Chicago northwest suburb for going on 20 years now, but I spent 3/4 of my life in and around Chicago and, truth be told, am still a Chicagoan at heart.
I bought the game mainly to see how the typical gangster view of Chicago would play out 'cause it always bugs me that mobsters and violence are all people seem to think about when they refer to Chicago. Yes, the game was simple and easily played but it was worth it to me to watch the cute, interesting ending which seems to try to debunk the usual Chicago scenario.