Which Is the Best Way to Fly to Hawaii With a Young Kid?

Apr 13, 2016

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As you probably know, I plan trips as far in advance as possible both in my mind and on the computer with actual dollars and points. If you are a family on a school schedule who is trying to leverage miles and points you likely do the same – or at least probably should do the same whenever possible. This strategy helped us secure suites using a combination of miles and points in Hawaii for next spring break, something we probably accomplished only because we planned so far in advance.

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Baby S @ almost 9 months

Now the time has come to start playing around with our flights to Hawaii. This is much harder in part because there are so many choices, and in part because Hawaii is just plain far from Texas. I’ve been loving the 2-3 hour flights we have been doing with Baby S since she was born, but I have no desire to permanently be bound by a 1,000-ish square mile radius, and by next year we will be more than ready to return to the islands that we love.

Time goes quickly in some ways, and Baby S will already be Toddler S by next spring break, and actually should be coming out of the hardest travel age range of about 9-18 months where the little ones are mobile but at times irrational, have limited communication skills, short attention spans, and are basically non-bribable. She will be the ripe old age of 20 months when our trip rolls around, and using my first daughter as a gauge (which is admittedly a questionable strategy), she should be content for a period of time with enough snacks, new toys, and videos. Additionally, she should hopefully be able to communicate and understand what is happening and why, at least to some extent.

Little C at 18 months
Little C at 18 months with her stuffed bribe

That said, from Houston to Maui is a 12+ hour travel day no matter what, and no amount of snacks or Mickey Mouse or crackers will last that long. There is no nonstop flight, and you will have to connect somewhere.

So, while I know the end game will be worth it, I am trying to come up with the best way to get us to Hawaii so we don’t all think this was a huge mistake somewhere over the Pacific, or spend way more than we can really afford either in dollars or miles.

My first Hawaii trip with Little C
My first Hawaii trip with Little C

The five main options as I see them are:

  • Secure Economy Plus seats on United going Houston – Honolulu – Maui or Houston – West Coast – Maui for a reasonable number of miles, potentially buying my ticket towards earning status and using miles for the others. We could do this via United and have free changes due to my elite status or use fewer Singapore miles and lock it in.
  • First class award seats on United, though this availability may well never appear or may only appear for less than desirable routings. This route would make Josh much happier since Hawaii is a bit over his “happy in economy” range. However, most of the first class seats United operates to Hawaii are either recliner style first seats or regular domestic first class seats.
  • Wait for a Hawaii fare sale on any carrier that drops the price to the $500ish per round trip ticket range and pull the trigger, though again routing may be less than optimal and our dates are fixed so waiting for this may be futile.
  • Connect in Dallas on American and have a straight shot from there to Maui, preferably in their 763 retrofit lie-flat first class seats. This option is insanely tempting, at least going one direction, and it looks like the retrofit first class seat maps are the ones displaying for our dates (I’ve lost track of the exact status of retrofitting the 763 fleet). However, thanks to our spring break travel dates the award prices are insanely high thus far for economy seats or the first class seats we really would love.
  • Book via Alaska using the $99 credit card Companion Certificate and/or miles and spend the night on the West Coast coming and/or going. The seats would be in coach, but no travel day would have a flight longer than 5ish hours, though there would now be four travel days if we did this coming and going.
American Airlines 763 retrofit seats

I would love if the perfectly timed first class United award saver seats opened up and we could lock them in for 60k Singapore miles each as we have done in the past. However, since we are very date tied with this trip, I think there is only a 20% chance of that really happening. Given all of our variables and our 20 month old travel companion, I am very interested in breaking the trip up with a stop or stops on the West Coast via Alaska at least one direction. Maybe the other direction we could splurge on the American first class seats if the price in miles isn’t too insane.

There are other nuances in these decisions such as being able to build in a “free one-way” if we book a round trip with United miles. Additionally, United first class would be more “worth it” if we are able to line up routes that have the lie-flat seats such as the Dreamliner routes from Houston to the West Coast, and even an itinerary connecting in Denver that has lie-flats the whole way.

There isn’t a clear winner at the moment, so I will just keep watching the various prices and award availability levels like a crazy person until an option presents itself as clearly being the best. Have you had to decide between similar options? What did you decide to go for?

The good news is that no matter what we choose I know what is waiting for us once we get there…



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