Rush Street, Chicago
Okay, so that was an awful pun, but to get a taste of La Dolce Vita in Chicago take a stroll down Rush Street. This is where the upper classes go to have dinner and hang out.
It is the trendy area to be in with stores (or should I say boutiques) and nice restuarants--some of which are affordable.
If you have the money, go to Gibson's Steakhouse--a Chicago institution where the rich and powerful eat (as proven by the Mercedes Benzs, BMW, Rolls Royces, Porches, and Ferraris parked on the street).
There is a Bentley Dealership that recently opened up in the area if you want to do a little shopping afterwards.