Quick follow-up: I am going on an actual trip to ORD for two days, so the complete itinerary is:

EWR-ORD (2 day stop)
ORD-IAH-LAX-HNL (5 hour stop)
HNL-SFO-IAH-ORD-LGA

This is a total of 11,270 PQM at 6.4CPM. The CPM over what an RT to ORD would be is 3.9CPM (this makes me feel better about the cost, because I would have been in ORD anyway). When I add the cost of buying the remaining 870 PQM, my total CPM to 1K is 7.5CPM, or 5.9CPM above the cost of the RT to ORD.

It could be better, but it could also be worse. I'm looking forward to dinner in Honolulu, and I'm keeping my hopes up for a few CPUs along the way. Thanks for everyone's help!