Wirelessly posted (BlackBerry8530/5.0.0.1030 Profile/MIDP-2.1 Configuration/CLDC-1.1 VendorID/417)

If you decide to fly ITO-ROC, then I would apply for the Chase/UA card, and use those miles for that trip (and perhaps for your inter-island flight, as well). You can still convert your Chase Sapphire Preferred UR points to Avios for the OAK/SJC-OGG nonstop on AS if that's how you decide to get to Hawaii.

But you might want to wait a few months before applying for the Chase/UA card, since you just got approved for a different Chase card (and have to meet those spend requirements, anyway).