Let me preface this by saying that I am no expert on how UC and UVA PhDs are specifically viewed by hiring committees, and I have not attended either institution. Common sense, though, tells me that they are both coveted, and I would not let a minute difference in somewhat arbitrary rankings make the decision for you (any school in the top fifteen or so is very presitigious).
You seem torn between the academic strengths of both institutions, and each has its points, so that's a bit of a wash. You could go back and forth endlessly comparing the two. If anything, I'd lean more towards the school that has the parts in place than the one that is planning to hire someone in the next couple of years. Plans can be deffered, especially in the midst of this financial mess.
What it would come down to for me is living very comfortably (relatively speaking) on $30,000 a year (an astounding stipend in the humanities!) in a place that is not expensive (Charlottesville) versus just getting by on less than $20,000 in a pricer urban center. I know that all great artists are willing to sacrifice for their art, but this seemes senseless. You could very well end up taking loans merely to survive at UC, and if not, you'd be living a pauper's life for at least six to seven years and then entering an always shaky job market. Since, by your own admission, both schools would be great fits for you, and both are highly prestigious, I would choose UVA, cutting down on financial stress and preserving my mental health and day-today happiness.
If you need one more reason to go south, reportedly the Hyde Park area of Chicago is not a particularly pleasant place to live (I'll let you do your own research to determine how you would feel about Hyde Park- tastes vary), while Charlottesville is a pretty town with good year-round weather compared to Chicago's challenging winters. Chicago does have more big-city excitement (duh), but Charlottesville has many cultural amenities for a city of its size and is a only couple of hours away from DC.
Either way, you can't lose. Congratulations and good luck with the decision!