Maybe I'm biased because I live here, but Chicago seems like a complete slam dunk for Amazon. We've got: good public transit, plenty of space for development, an educated workforce with a a decently sized tech talent pool already developed, easy draw from Big 10 schools and the University of Chicago, and a (relatively) low cost of living when compared to comparable cities. Yes, the state and city have financial problems, but watch how fast the gridlock disappears when an opportunity like this presents itself. As I said in another comment, the city has been really good at getting companies, both from the suburbs and from out of state, to setup headquarters in the loop.