Originally Posted by Totoro

WN RR R/T awards are booked as 2 O/W trips, so you can book each leg as you wish. Happy travels!

Originally Posted by irabk

Southwest does not have issues with "open jaw" tickets because you can book one ways for each flight. The experienced SWA FT'ser will ONLY book one ways, in case of a fare change. That way you can rebook the flight that has gone down, and not impact the other flight.

Back to your specific issue. You should book 2 one ways with your award ticket. Actually, your award ticket is two one way flights, an A & B half. You do not even have to use both A&B on one trip. If you find a cheap fare one way, you can pay for that and save the other half for another trip. You can also book two people one way, using both A&B, and pay for the other flight.