Friday, June 24, 2022

When Is The Best Time To Buy A Ticket To Hawai'i For Christmas? (It's Already Too Late, Isn't It?)

I've been procrastinating on buying a ticket to see my sister graduated in Honolulu.  She walks in December, and the family has decided we are all going to make a big family vacation out of it.

It's been hell.  The logistical nightmare of 1) flying off the mainland 2) to Hawai'i 3) around the holiday and 4) staying upwards of two weeks (maybe more) to sightsee and have fun means we need to splurge on 5) accommodations and 6) transportation.  Add to it that this family is as dysfunctional as any otherwise high-functioning group of biological connected members can be has produced a long slog of not thinking about it, burdening one person (my sister) to make all the plans, and bitching about any plans my sister does make.  The back-and-forth about what to do, let alone where to stay, how long and how much, makes me wish I could just fly in for a weekend, see her get her diploma, then go back home.

What is coaxing me to think about this vacation more, even if I'm not doing anything, are the parameters set up by my other family members.  What I mean by this is my brother (and his family) and my parents have finally booked flights to get to Hawai'i.  Knowing when my brother is going to Honolulu and when he's flying back gives me good enough reason to find flights that don't depart and arrive on the same day.  I might have to pay more, but the awkwardness of boarding the same flight but not sitting together is worth it.

I did, however, wait on my folks.  There was a possibility that they would really want me to, instead of flying to Honolulu, fly to Las Vegas instead, and from there all three of us would head to Hawai'i.  I think that idea would have been viable if there were dirt-cheap prices on such a flight; it would then be worth it, the thinking goes, to hopscotch from MSP to LAS and then to HNL.

Alas, early this week I saw that my parents booked a flight to Honolulu several days before my sister's big day.  They did not consult me on this purchase, so I think there is no expectation for me to be on the same flight as them.  Moreover, I do not want to miss that much time from work, so I have another built-in excuse to just go off on my own.

And beyond that, when I called Mother about this flight they purchased, she said that she is waiting on flights back to the mainland (I'm guessing Vegas, though I'm not 100% sure about that) because she found two tickets back right after Christmas too expensive.  She thought she would stick around Honolulu and hang with my sister and brother-in-law through New Year's ... and maybe beyond.  That actually is a good thing for me when it comes to planning.  I had thoughts about spending a day or two or more in Las Vegas with my folks ... but that would have been right after the vacation in Hawai'i.  Also, I don't have the paid time off from work to spend, well, upwards of a month, and even if I did, I don't think I would want to.

So that seemingly frees me to find a flight back home on my own.  Pair that with flying to HNL solo as well, and, well, I have the freedom to get there and back however I please.  That clarity, or at least the limits against which I know when I should fly there and when I can fly back, spurs me to action.

Sort of.  Price is nominally a concern, a big one.  But I have it in my head right now that I really, really want to break up the flights to and from Hawai'i on a non-direct flight because I want to accrue as many points as I can on the airlines with which I have a frequent flyer number: Delta and United.  So right now (well, not right now, I'm going to bed after this) I have set up alerts (or at least I think I have) for round-trip, non-stop flights to and from Honolulu, one-way, multi-stop flights to and from, and everything in between.  I will bite as soon as these alerts tell me the prices they see are the lowest they'll be.  That's all I'm waiting on.

Unfortunately, this is Hawai'i for Christmas.  I have seen that travel experts believe the lowest fares to Honolulu are at their cheapest 1-3 months before the trip, although I wonder if the international "Goldilocks window" of 2-8 months would be more appropriate for Hawai'i.  At any rate, I'm procrastinating because the prices I've seen weren't cheap enough.  Unfortunately, I don't think I've seen prices that low since.  I'm going to wait a little longer because hey, in for a penny, in for a pound.  But I fear that prices will only go up from now, and I'll have to pay even more.

Knowing when to buy a plane ticket at its cheapest is a dark art.

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