Originally Posted by PHLGovFlyer
Hawaii is a tough destination for award tix. Last year I did a trip to HI using US miles and flying entirely on UA metal. I had to book at 330 days ahead and I still needed to flex my travel dates by a few days to get the awards. I also had to fly mainland to Oahu, even though my destination was Kona. There were no outbound award flights to Kona open for awards. I managed to get Kona to mainland on the return. The open jaw is not such a bad deal since you get to see more than one island and the inter-island flights are only about $80 per person one-way IIRC.
I tried various methods (online, US phone agents, UA phone agents just to see if they showed inventory for their own members), and in the end the US phone agents came through for me.
Also some folks on FT and the res agents I spoke with suggested trying again a few months later since seats do sometimes open up as dates get closer. You just have to be flexible about dates.
My experience last year was almost identical to yours. We were flying 3 people on UA metal using US miles, trying to fly into OGG, and return from LIH. 330 days out, with some flexibility in June dates, we were able to first book IAD-ORD-HNL outbound (nothing available into OGG) and LIH-SFO-IAD return. Then a few weeks later we got our desired outbound IAD-SFO-OGG (with a very nice US agent who did NOT charge us the change fee for a new itinerary.) Then a month later we changed to the same itinerary with a July departure. Then several months after that we were able to book an earlier IAD-SFO flight on the outbound, for a better connection in SFO. Ultimately, our only compromise was a trip that was one day shorter than we wanted.
iflyjetz4work, here are several points to consider: First, each change we made should have freed up 3 seats on the flights we were holding. In theory, those could have been booked by someone who was watching for new availability. Second, the final change, which took place in February, I believe, was accomplished when a block of award seats came available. (United.com was suddenly showing 9, IIRC.) I saw those online, called US immediately, and made the change. So yes, additional seats do come available. Third, the available inventory we saw on the flights from the mainland to HI was often only 2 seats, even 330 days out. And fourth, just to make life more difficult, I was told by several US agents that US is not given access to all the award inventory that UA has available.
Other FT members should be able to offer more first-hand advice, but I did find that one way to simplify the hunt is to first look just for the flights that are the hardest to get, i.e. between the mainland and ANY island in HI. If you can get to/from the mainland and HI, it should be much easier to find a connecting flight from your home to the gateway city. And no matter where you want to go in HI, as long as you can get to ANY island on award points, you can always book an interisland flight to the island you really want. But you will probably need to be flexible on your dates, especially now that you're well inside the 330 day window.
Best of luck. I hope this helps.