We go to Maui (OGG) every year (for the past 10 years) for the holidays. We fly UA from CID. We have found the best strategy to book as early as possible. We already have our tickets for this coming Christmas.
If fares go down (sales usually come in September, but last year it was October) then we refare if possible. We also book our hotel a year in advance as the place we stay is usually sold out by May. 12/26 is the busiest day to go to the islands. When we have gone on the 26th the fares never went down due to sales and forget about upgrades on the 26th also.