Telltale $99 Southwest Hawaii Sale | Summer and Fall

Telltale $99 Southwest Hawaii Sale | Summer and Fall

This is the first step in airline realignment to the reality of fewer west coast to Hawaii travelers ahead. And while Southwest has had many $99 sales and even some lower Hawaii deals, we didn’t expect this price point to return for the second half of 2023. But it has, and this won’t be the last of it. Until now, the other airlines were hoping to keep prices significantly higher, and on the routes on sale today, Hawaiian, Alaska, and United still charge substantially more.

Is another $99 Southwest Hawaii 2023 price point about to be set?

It appears that the $99 price will again be needed to drive more Hawaii air travel from the west coast. We think that Southwest is right, and we’ll see those fares, and even lower ones ahead, from Alaska, Hawaiian, and Southwest. Get ready for more of that to follow.

$99 Southwest Hawaii Sale | Summer and Fall

Southwest is putting its toe in the water to see how the $99 fare will work. So it is limited for today, but probably not for long.

Travel during August, September, and October. Use Southwest’s Low Fare Calendar to find available dates.

  • San Diego to Kauai $99 one-way  ($199 round trip)
  • San Diego to Kona $104 one-way ($208 round trip)
  • Many other Southwest Hawaii routes are on sale at $119-$124 each way.

Don’t miss out on these $99 airfares coming on a Monday rather than a typical “Hawaii Sale Tuesday.” That’s somewhat further indication that something is up here.

These Southwest Hawaii airfares are the total price each way, including all taxes and fees. They are widely available at the time of publishing, which is 10 AM Hawaii time on June 5, 2023. Do not wait, however, then expect these to be available beyond today! 

Today’s Southwest Hawaii airfare sale is valid in both directions, starting on the mainland or in Hawaii on the routes listed above. Availability varies by route and day of the week.

Late summer and fall are a perfect time for a Hawaii vacation! Join us and luxuriate under the Hawaii sun. The weather doesn’t change much here, and you can still expect warm days and nights. And great ocean temperature as well.

More details on booking today’s Southwest Hawaii airfare sale:

  • Airlines change fares up to 5x daily. Availability will decrease as tickets are purchased.
  • Don’t wait to buy these later, as they will be gone.
  • You can commence your travel either on the US Mainland or in Hawaii.
  • Prices are one-way and include all taxes and fees.
  • Book online only – these fares are not available by phone.

Will more of the lowest Hawaii airfares entice your return to Hawaii?

Beat of Hawaii photo of Southwest aircraft at Lihue, Kauai.

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8 thoughts on “Telltale $99 Southwest Hawaii Sale | Summer and Fall”

  1. Wait… Wait … Wait…
    I think we all remember that BOH predicted fares were going to be sky high for the summer?
    So what happened?

    1. They certainly are with Hawaiian. I’ve been waiting for them to go down and they have been doing just the opposite

  2. Aloha! Just as an FYI – Southwest Airlines seems to be having a problem with their website. No matter what I try to book a flight in either September or October, I get an error message and am unable to even see what may be available. I’ve also tried using different departure dates and airports (Las Vegas, San Diego, Los Angeles, Burbank), I get the same error message. So good luck to everyone else trying to take advantage of this sale. Mahalo.

  3. Sure wish summer airfare on Hawaiian would go down. You couldn’t pay us to fly on Southwest anywhere, especially to and from Hawaii

    1. Hi Mike.

      A couple of us editors are flying Southwest from Hawaii this week and will report on it. The first time was better than expected.


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