Originally Posted by
JJeffrey
Honestly your chances of a sticker upgrade as a Gold to HNL are extremely slim, so I wouldn't plan much around that as your chances are bad regardless of which hub you connect through.
For a miles/copay upgrade, the 15k + $175 covers up to 3 segments each way. Looking at ExpertFlyer I actually see upgrade space on 8/18 for MIA-PHX-HNL and 8/26 HNL-PHX-MIA. So if you could get your flight booked now you could call AA and they could confirm your upgrade immediately both ways, all segments, for 30k miles + $350.
depending on when you go, this can be really tough to clear. I booked a trip last summer for this past February, and first through Dallas (to/from both Honolulu and Maui) were practically sold out 6 months in advance.