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A few weeks ago Scott posted about The Cheapest Ways to Get to Hawaii.

I recently came across another sweetspot to Hawaii I wasn’t aware of. It costs just 17,500 Alaska miles to fly Alaska Airlines between the mainland United States and Hawaii. And for a little more (20k one way) you can fly Virgin America from a couple west coast cities to a couple different Hawaiian islands.

And since we’re talking Alaska miles, you can book one free stopover per one way. That means you can book a roundtrip with a stopover in each direction (or a free one way!) for just 35 or 40k miles. That’s a great deal.

Waikiki at Sunset
Waikiki at Sunset

Redeeming 17.5k Alaska miles on Alaska Airlines to Hawaii

Any of those flights should cost just 17,500 Alaska miles + taxes. If you don’t live in one of those cities, you can add a connecting segment and still maintain the price as long as it’s on Alaska Airlines, the lowest level award price, and doesn’t fly farther east than St. Louis (thanks to reader Beth for pointing this out! I previously thought it was Dallas).

That chart shows the price to fly Alaska Airlines between the mainland and Hawaii. The economy price has a range, 17,500 to 30,000. The farther away you get from Hawaii the higher the price, and it appears the farthest east you can get without breaking 17.5k is St. Louis.

Here is a flight from Dallas for just 17.5k…

…but when I added an Alaska flight to Chicago it priced at 30k.

Granted, you could fly straight to Honolulu from Dallas for 22,500 Alaska miles non-stop on American, so it probably isn’t worth saving a few thousand miles to fly the schedule above. The 17.5k sweetspot to Hawaii is more useful for those that live on the west coast or near it, in a destination Alaska flies to. 

Redeeming 20k Alaska Miles on Virgin America to Hawaii

This award will be useful to less people as that price only applies (as far as I can see) to Virgin America flights between San Francisco or Los Angeles and the two destinations they fly to–O’ahu (Honolulu) and Maui (Kahului).

Adding A Stopover or a Free One Way

Alaska Airlines awards can have one stopover per one way award or two per roundtrip. There is no limit to the length your stopover, and your stopover could be your home airport which means you can get a free one way award (more on this below).

On the way to or from Honolulu on an award flying Alaska Airlines for 17.5k, you could easily build in a stopover in Anchorage, Oakland, Portland, San Diego, San Jose (CA), or Seattle as those are Alaska gateway cities. For example, instead of just connecting in Seattle like in the screenshot above, you could hang out there for a few days.

Don’t want a stopover? Book a free one way instead. A free one way is a separate trip, separated by days or months from your main trip, that uses your home airport as the stopover and adds zero extra miles to the cost of your award. Your free one way can go TO your home airport BEFORE the main award or FROM your home airport AFTER the main award. Utilizing one of these cheap Alaska awards to Hawaii and then tacking on a free one way is a great way to maximize the free stopover feature. Just add a free one way somewhere you plan on traveling to in the future, since you’re not inhibited by the length of your stopover beyond the fact that you can only book flights 11 months in advance.

Let’s say you actually live in Seattle but plan on traveling to Los Angeles in the future. You could make the following flight your free one way, tacked on to the beginning of your itinerary, before your main trip to Hawaii.

That flight would essentially be the return leg of a separate trip prior to traveling to Hawaii, but you don’t have to pay anything for it!

If you priced out the whole roundtrip (Los Angeles -> Seattle ~3 month “layover” -> Honolulu -> Seattle) it still costs just 35k total (17.5k in each direction).

You could also book a stopover in one direction, and a free one way before or after your trip if you didn’t want two stopovers on a roundtrip. Don’t want any stopovers? Book two free one ways on a roundtrip. For example, Los Angeles -> Seattle ~3 month “layover” -> Honolulu -> Seattle ~3 month “layover” -> Boise would still only cost 35k!

If you have the organizational foresight to be able to book your trips this way, there’s a TON of value to be squeezed from Alaska miles.

How to Search for Award Space When Including a Stopover

If you want to include a stopover on your Alaska award, you’re going to have a much easier time searching segment-by-segment. For example, take the most recently mentioned award: Los Angeles -> Seattle ~3 month “layover” -> Honolulu -> Seattle ~3 month “layover” -> Boise. First search for the segment with less available award space, which is usually the longest segment and in this case is Seattle > Honolulu, and then the others.

Once you have found award space for all of your desired segments, search using the “Multi-city” function by ticking the Multi-city box (as well as the “Use Miles” box). If navigating from the home page, you’ll have to click All Search Options to get to advanced searching options.

Going straight to multi-city searching is going to present issues like the ones described in Troubleshooting the Alaska Free One Way Search.

How to Get Alaska Miles

SPG points transfer 1:1 to Alaska miles, and both of the Amex SPG cards (personal and business) come with record high 35k bonuses until April 5.

The Alaska Airlines Visa Signature cards (personal and business) each come with 30,000 Alaska miles after meeting a $1k spending requirement and paying the $75 annual fee.

You can also buy Alaska miles, sometimes with pretty decent discounts.

PRO TIP: You can convert the bonus from Chase’s Marriott cards into a hefty amount of SPG points thanks to SPG and Marriott’s new-ish relationship. Three Marriott points converts to 1 SPG point. You’ll earn 83,000 Marriott points after meeting the minimum spending requirement on either card, which converts to over 27,000 SPG points. Even if you’re over Chase’s 5/24 limit, that rule is known not to apply to the Marriott Business Premier card.

Bottom Line

For 17,500 Alaska miles you can fly from many destinations on the western half of the United States to Hawaii one way in Alaska Airlines economy. For 20,000 Alaska miles, you can fly Virgin America economy from Los Angeles or San Francisco to O’ahu or Maui.

It’s easy to accrue Alaska miles as you can sign up for one of their co-branded Bank of America credit cards, an SPG card (SPG points transfer to Alaska), or a Marriott Card and convert those points into SPG points.

Have any of you ever booked Alaska or Virgin America flights to Hawaii with Alaska miles?

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