Planning a honeymoon over the holidays in December 2016. Flying first to Fiji, then on to Auckland, then flying back Auckland-ORD on Jan 1. I'm pretty determined to fly First/Business the whole way.

While United isn't a great option for the flight to Fiji, we can fly Air New Zealand to Auckland, then fly United back on its new 787 flight (seems more comfortable than ANZ's 777).

Tickets are expensive, obviously. But United's mileage upgrades seem like a good deal. I have no miles w/ United, but my father has a ton. Can he use those to upgrade my fiancee and me? I'm used to Delta, where that's not possible without paying exorbitant fees.

Question 2: I'm silver status on Delta, and since I'm moving to Chicago soon I'm thinking about getting my status matched on United. Is that possible, and would that help with the honeymoon planning?