Erik, after C'Springs don't know if your son will like the Midwest "climate", etc. but, given the circumstances, I think you are making some wise educational choices. There is quality (of education and social environment) to be had in schools like those you are visiting - I happen to have special personal liking for Luther.
From O'Hare you are probably best just setting off westward rather than trying to squeeze something in - for Chi. I'd wait until you have time to pick/choose and do the good places justice. Having time to leisurely look at college towns/environments seem more valuable in this case.
Might be good to have some great CDs, books on CD or good conversation topics planned as the drive west from Chicagoland is boring when compared to your Rockies.
It is great that you are doing this - fortunate son.
