Originally Posted by guv1976

It sounds like what you are looking for ideally is a "triangle" trip (A to B to C and then back to A), not an "open jaw." (If you preferred to travel from PDX to LAX by car or train, then you would be looking for an open jaw.)

Although I can't offer any help to you with using your current credit-card miles, I would ask: Is this a one-time-only itinerary, or one that you plan to repeat in the future (to visit friends, family, etc.)? If this is a trip you plan to make more than once, I would suggest that you see if any airline would permit you to fly your desired "triangle" itinerary on a round-trip award, making an en route stopover (i.e., midwest-LAX with a stopover in PDX, and then LAX to midwest; or midwest to PDX, and then PDX-midwest with a stopover in LAX).

Unless the rules have recently changed, American Airlines permits one open jaw and one en route stopover on domestic award tickets. (Other carriers sometimes permit on or the other, but not both.) AA has been known to be pretty liberal about allowing stopovers on their domestic award tickets. I was once able to fly NYC-LAS; then LAS-RNO (connecting in LAX); and then RNO-NYC on a single award ticket, staying over in both LAS and RNO. Whether your particular itinerary would qualify I do not know. If you identify any carrier that would be good for your future travel plans, concentrate on that carrier. Citibank is currently offering a variety of AA credit cards fee-free for the first year, with 25,000 bonus miles if one charges $750 to the card within the first four months of card membership.

Hope this is helpful.