Snickers, I know what you're saying about the blue collar feel of Chicago. Visited a couple times and always got that vibe from the city (in a good way). Not that I have any experience with Chicago mobsters (or NYC mobsters for that matter) but from pictures they always seemed more laid back and less flashy than their NYC counterparts which is probably mostly due to the east coast generally being flashier. Not sure though...I'm sure the members who have neighborhood experience can add more insight.