As far as landing a position at any given hospital, I think it would depend on the institution.
You would probably have a more difficult time getting a job at one of the more prestigious, academic hospitals (depending on your credentials of course) than you would, say, at a private suburban hospital. Of course most anywhere you will go, the further you get from the city and into the rural areas, the easier it becomes in general to land a position.
As far keeping that job, I have a friend who is a recent EM residency graduate who will be living in the Chicago area (family), but will actually work in Indiana. I don't know all the details, but he says that the malpractice environment in Illinois is too prohibitive for him to want to get a job closer to his home.