A lot of good advice in this thread but I'll just throw in my $0.02
- Hawaii is generally not a destination where waiting for a 'last minute deal' would be a smart strategy. Typically in Canada the destinations that are occasionally discounted by the tour operators at the last minute include: Mexico, Dominican, Cuba, Jamaica - destinations that are popular for 'all inclusive' travelers (ie: include food + drinks).
Occasionally however, WestjetVacations will discount their Hawaii packages, so they would be worth a look 1-2 months before departure. They generally don't move drastically in price at the last minute though..
On American based sites, such as Expedia/Travelocity, they are simply bundling the latest real-time airfare prices from the major airlines with their hotel inventory. The major airlines never discount last minute flights (can be quite the opposite, with prices skyrocketing) so a last minute strategy would not work in this case either.
- Flights from Calgary to Honolulu (HNL) bottom out fairly consistently at around $525-$550ish roundtrip after taxes these days. In general, anything under $600 is probably a good deal for most people. There hasn't been a fare in the $400s (roundtrip after tax) since May of 2011.
- Honolulu is always the cheapest to fly into, but Maui (OGG) is usually just $50-$100 more roundtrip. Kona (KOA) and Kauai (LIH) are generally a little more than that.
- Airfares to Hawaii are relatively consistent year round. The biggest influence on price is likely to be anything around peak holiday periods. The further one can get from the dreaded December 21 to January 7 date range, the better.
- As with a lot of destinations, I wouldn't be overly afraid to watch fares up to about 8 weeks before departure.
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