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.
I want to know how Chicago trading company compares to these two and I dont know much about the place.