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Flying to Hawaii is a real commitment. From the mainland, it’s thousands of miles and many hours in the air. For much of the United States, Europe is actually closer than our 50th state sitting out in the middle of the Pacific Ocean. That said, Hawaii is absolutely worth it for our family, even factoring in the great distance you have to cover to get there. In fact, as cliché as it sounds, Hawaii is probably my own personal favorite destination.

Hawaii (and specifically Kauai) is a magical place
Hawaii (and specifically Kauai) is a magical place (Photo by Getty Images)

However, we haven’t yet taken our youngest daughter to our favorite islands because the flight schedule from the middle of the country is a little grueling. On top of that, the time change from Middle America to Hawaii is practically guaranteed to cause toddler sleep-schedule chaos and middle of the night wake-up calls.

But the time has come. We’re actively booking a trip to Hawaii for not just our family of four, but extended family members as well. This will not only be my three-year-old’s first time flying to Hawaii, but my parents’ first time, too. It’ll also likely be their only time to visit as they vastly prefer multiple shorter trips within the continental US rather than longer (pricier) adventures.

Soon it will be time to fly to Hawaii with both girls!
Soon it will be time to fly to Hawaii with both girls!

So, with all of those variables in play, I had to again decide the best way to fly with kids to Hawaii while relying on award tickets as much as possible. Hawaii airfare deals are a dime a dozen these days, but sadly, that’s not usually true on peak summer travel dates from the middle of the country. I’ve flown practically every reasonable way possible to Hawaii over the years, and there’s no doubt in my mind as to what route is the best when little kids are involved.

One of the many ways we have flown to Hawaii over the years
One of the many ways we’ve flown to Hawaii over the years.

The best way to fly with kids to Hawaii

When you’re flying to Hawaii with kids who are four or five years of age and under, the best way to get there is to stay on the West Coast overnight both coming and going. This is how I got to Hawaii with my first daughter when she was three years old, and it’s the way I’ll be getting there with my second daughter when she’s roughly the same age.

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On Kauai with my first daughter as a three-year-old.

Staying on the West Coast before continuing on to Hawaii with little kids has many advantages. An obvious one is shorter travel days. Our last trip to Hawaii took about 23 hours door-to-door flying Houston (IAH)-Dallas (DFW)-San Diego (SAN)-Maui (OGG) on American Airlines miles — and that’s without any significant delays or issues. Our then 7-year-old handled it mostly like a champ (though she did collapse a bit on the sidewalk between terminals in San Diego), but pushing a younger kid through that grueling schedule isn’t high on my travel wish list.

Baby step into the new time zone

In addition to shorter travel dates, by stopping on the West Coast, you get the benefit of adjusting a bit to the time zone changes as you go. Hawaii is five hours behind Central time, and that means a kid who normally gets up at 6am or 7am may very well be waking up at 3am or 4am, if not earlier. We’ve dealt with this in Hawaii many times, but it’s a little easier spending the night on the West Coast and knocking out a bit of the adjustment by baby-stepping into Hawaii’s time zone.

This time around, we’ll be staying in San Diego on the way to Hawaii, so we plan on seeing a little bit of the city on the day we arrive, which is a nice added perk.

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(Photo by Peeter Viisimaa / Getty Images)

No red-eyes home

As happy as I am to stop for a night on the West Coast on the way to Hawaii, I’m even happier about it when coming home. Flights from Hawaii to the mainland are all red-eye overnight flights unless you fly to the West Coast. Even then, only a handful of departures leave during the day.

If you have the miles (or cash) for lie-flat seats to fly back home from Hawaii with the whole family up front (and I’ve done that), then the red-eye isn’t that bad. However, lie-flat awards seats home from Hawaii are pricing close to 100,000 miles per person more often than not these days, and it just isn’t worth it to spend close to a half-million miles just to fly home in lie-flat seats.

I’d rather skip the lie-flat seats, save the miles, leave Hawaii in the morning and land on the West Coast before bedtime. We’ll sleep near a West Coast airport that night, get a little readjusted to the mainland time zones and then continue home the next day while sparing our three-year old (and ourselves) from the red-eye flights.

How to book the best flights to Hawaii

There’s no one way to book flights to Hawaii that spend the night on the West Coast, but I’ll walk through some options…

Take advantage of stopovers

Alaska Airlines has an extensive network to Hawaii from the West Coast, and it allows stopovers on awards. Additionally, the Alaska Companion Certificate you get each year with the Alaska Airlines Visa Signature credit card can easily be used with a built-in stopover on the West Coast. You can learn more about the Alaska Airlines credit card in our review.

My immediate family will be flying back using Alaska Companion Certificates from Lihue (LIH)-Seattle (SEA)(overnight)-Houston. With the Companion Certificates, you can pay for one fare and get the other for a little over $100 (or less with some versions of the certificate). Several flight options that displayed for us on Alaska included an overnight on the West Coast at no additional charge.

My parents will be flying home on a different day than us, and they’re using American Airlines Saver awards that have a built-in overnight in Los Angeles (LAX). For 22,500 miles each (with an extra 10% mileage rebate for having the Citi / AAdvantage Platinum Select World Elite Mastercard), they’ll fly from Lihue to California, sleep in a real bed, and then continue home to Texas the next afternoon. Spending around 40,000 American miles in total for two tickets plus the cost of an airport hotel near LAX is a much better deal than spending 200,000 miles to fly in a lie-flat seat home — which is the only other option I’m interested in when coming home from Hawaii.

Book two separate tickets

If you can’t build in a stopover on the West Coast to or from Hawaii all on one ticket for a reasonable cost, you can always book two tickets. You can book one from your origin to the West Coast and then another from the West Coast on to Hawaii. There are some risks in this strategy in the event of weather or cancellations, but with a built-in overnight, you’re safe from having run-of-the-mill delays wreck too much havoc on your plans. Your only real risk would be outright cancellations of the flight or flights on the first ticket, causing you to miss the flight on the second.

Risks accounted for, this is how we plan to get to Hawaii this time around. We’ll book one ticket to San Diego, maybe even on a low-cost carrier. Then the next day, we plan to fly Hawaiian Airlines from San Diego to Honolulu (HNL) on an entirely different ticket. This actually makes sense cost-wise, as you can get tickets from Houston to San Diego and then San Diego to Honolulu for reasonable cash prices.

This may become an even better strategy with Southwest flights to Hawaii launching in the near-term, though it will depend on how those tickets and flight times look when they become available.

While it won’t solve all our problems in the event that we misconnect our second ticket, we’re being careful to purchase our airfare with a credit card like the Chase Sapphire Reserve that has solid built-in trip delay protections.

Maui with my oldest daughter in 2017.

You don’t have to spend the night on the West Coast to get to Hawaii, but if you’re flying with little kids, it truly is the best way when you’re coming from the middle or eastern half of the United States.

All photos by the author unless otherwise noted.

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