Just so you know, if you pick something up out of skedminus-, you can't drop it. I was also told that you could trip trade out of domicile, but I had to call crew support still. I think that program still has a long ways to go to be all that it was touted to be.
Denver is relatively senior. I would be six months before getting after you start class. So figure two months in class and four months in MKE or ORD. I would stay in MKE because we do that flying and ORD-DEN would be a tougher commute. Good luck and bring your friends.