Off-peak dates (cheaper in $ and cheaper in airline miles if you have enough) Hawaii: Jan. 12 - Mar. 8; Aug.22 - Dec.15 (source: American Airlines)Personally, I feel Hawaii is best in August when crowds are beginning to shrink but the heat is still overhead. Late August would be perfect!
September and early October are great times to look for good discounts on going to Hawaii and for lower hotel costs. This is a "shoulder season" when kids have just gone back to school so hotels are much more welcoming. My favorite airline is Hawaiian Airlines.
Sign up for their emails to learn about specials to the islands. As for learning about the islands themselves and things to do there, check out hawaiibestravels.com for some good information about things to see and do for each island.
I am not sure when the best time is to buy the ticket is. I do know that Delta was my favorite for flying there. I flew on them to Honolulu from MSP and was in Business elite class.It was reasonably priced for the amount of comfort you got, I slept like a baby.
I also watched a few movies while eating. The food was great I got a bowl of pasta with a cream sauce which was surprisingly good, and then a sandwich for lunch.
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