Quote from mdl060374:
If the two job openings/offers are for the same type position, I would honestly just go with the place you would like to live..
You stated its Chicago, so give it a shot (assumming thats the offer.)
If you already have an offer from one, why not just take it?
I am a bit confused, b/c you yourself admitted they are of the same calibre, and dont have a huge prefrence for either city.
So going on that info you provided, it sounds like the choice is already made?
Good luck anyway.