Thanks for the input all!

It seems that I would also be able to leave later from RIC if I flew RIC-IAD-DEN-SJC, which would be a good thing. I also have always liked IAD, and the transfer time at IAD and ORD works out to be the same. The IAD connection also would give me less time on an RJ, which is hard to complain about.

Thanks for the advice! ^