Originally Posted by
view-with-a-room
If T or U level are available the ticket is a $150 ticket so not a concern. Generally easier for me to book the ORD-Japan and sort out how to get to ORD after the fact. Booking two tickets provides more flexibility. If AA changes the flight I only need to deal with AA. If JAL changes the flight I only need to deal with JAL. The goal is to keep the JAL flight intact at all costs...
But if AA fails to get you to ORD in time for the long haul, you have no flexibility other than to cancel ORD-Japan.
Paying for a flight that you can get for free is a tough sell to me. Best case scenario, tack on the U/T ticket the day before, as long as available with layover in ORD of less than 24 hours.