I'm not from the northeast at all and have no skin in this game, but I think I agree that Pitt shouldn't be considered mid-tier. It's definitely a rung above places like Rush...not that Rush sucks at all, but it's more like a place you go if you want to be a hospitalist, or make some connections in Chicago, but not necessarily try for fellowships at "academic" type places.
As far as the OP's question, I think we need to know more about the OP. Personally, I think the importance of atmosphere of a program (i.e. how does department and GME office treat residents, is there decent food on call, decent parkin, how will your fellow residents and the attendings treat you, etc.) is very underrated. If you can find out something about THOSE things and maybe decide based on that, you may want to consider it. I don't personally think that those 3 institutions are far enough apart in terms of "prestige" that it will affect your fellowship prospects a lot one way or the other. I do think that if you're going to plan to stay in New York long term, it might be better to do residency there. Similarly, if you want to get a hospitalist job or fellowship in Chicago later, or elsewhere in the Midwest, then being at one of the Chicago programs might be helpful.
There was some sort of financial badness going on at U of Chicago a couple of years ago. Not sure if that has resolved, but I know they did lose some faculty at that time. Still, there's no doubt it still has a good academic reputation.
