Remember how obsessed I was with ancient Roman history when I studied abroad? (Refresh your memory in my archived posts.) Brit is probably just as obsessed with Chicago history and has quickly turned me on to it. She's got me reading books like Sin in the Second City by Karen Abbott and it's uncanny how similar the cities actually are.
Chicago is notorious for its crime and corruption, and much like Rome it has many mob connections. Both cities have rich traditions of underworlds, secret groups, and dark sides exploited in books and movies. In Rome, "que bordello!" is uttered to comment on something being wild (literally, a whorehouse). Chicago was home to one of the most illustrious bordellos in America at one point.
The Eternal City and the Second City of course share less corrupt things in common as well: an intense passion for food, varied and diverse neighborhoods, sports rivalries (Lazio v Roma soccer/Cubs v White Sox baseball), and funky street smells (hot garbage, piss, dog) for example.
My apartment reminds me of living in Rome as well. I stand on my front porch and watch traffic on my one-way street, I hear many conversations from the building next to me through my window, my downstairs neighbors are always smoking, and I'm only a little way from the train into or out of the city. My neighborhood is residential and has an old working-class feel. It makes me want to write a lot.
The biggest difference between my two lives is most likely having fairly efficient public transportation and streets on the grid. It's far less difficult to get lost or be late here. Sad day.