Originally Posted by
TheMilesProfessor
Why not Hawaii? It's over on the West coast side, warm, romantic and probably has some availability in May. United Airlines will let you do a stopover when booking a miles trip to Hawaii so you can do Dallas - Hawaii - Oregon - Dallas all in one itinerary.
You also noted United flies to Oregon.
+1.
You'd be redeeming one round-trip using US miles and one using UA miles, likely both on UA metal through SFO. I can't speak to how loose the stopover rules are with a small airport in Oregon involved...whenever I've done a stopover, it's been along a logical routing for the round-trip. Maybe you can work PDX in there? The UA/US experts will know better.
Hawaii's a good choice though. When we went in May a few years back, we were able to find our desired airline/hotel awards. I don't get the sense that Hawaii ever has a truly off-peak season, but going in May beats trying to go to Spring Break, Christmas/New Year's, etc.