I wasn't looking for, book this route at this price, kind of suggestions. More of United runs lean on xyz route, or stay away from this route. I have read the FAQ's and will admit that I have a lot more to learn, I think my initial post was also to reassure myself, that even though my family gave me the strangest look last night, it still was a good idea.
I was able to find ORD->IAD->MCO->DEN->SFO->ORD, 24 period of flying, but no hotel for $530. Little more than I want to spend, but gets me around 5,700 miles.