$99 Alaska Airlines Hawaii Deals | August Til November

Alaska Airlines Hawaii deals today including California, Portland, and Seattle. Plus their new automated pricing

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274 thoughts on “$99 Alaska Airlines Hawaii Deals | August Til November”

  1. Thank you so much for providing this excellent resource. I watch your site regularly and subscribe to your emails for the latest updates.

    We have travel plans to Kauai from July 19-August 2, with flexibility to shift 1-2 days if needed. We’ve been holding out for Southwest, but with the ongoing 737 Max troubles we’re getting nervous they’re not going to launch Kauai service in time, and fares on the other airlines are creeping up.

    We can depart from any of the Southern California airports. LAX and San Diego seem to have the best options so far. Do you recommend waiting for Southwest (or more deals from the other carriers)? Or are the current fares as good as we’re going to see for this July?

    Thank you!

    1. Hi David.

      Sorry, but we just are not certain as of this moment. If May 1 comes and goes without any further announcement from SWA, then we can assume this might drag out for a while. We’ll update on that as soon as we have more info.

      Assuming no Southwest, low $500’s for your exact dates or come and go a day earlier to save $100. Good prices, and might not be worth waiting for the unknown, unless you have a stomach for that sort of thing.


  2. Hello,

    I am in the beginning stages of planning a trip to Hawaii in early June 2020. This post makes it sound as though April-May is usually a good time to book tickets for early June of the same year – am I understanding correctly? Also, I know things are in flux with Southwest and other airlines right now, but if you have any suggestions or predictions for the best/most affordable way to get to Lanai or Maui from STL airport they would be much appreciated. Thank you!

    1. Hi Jamie.

      To avoid the summer high season prices, you need to plan to have returned to the mainland the first week in June. So that would be June 4. After that, fares will go up the following week by perhaps 30%+ and the following week by much more. If that works for you, then target buying tickets about three months in advance. If, however, you’re traveling later than that, then you may want to start the purchase process more like 11 months in advance. That includes air, accommodations and car. SWA isn’t going to be a part of this, since we don’t expect them to offer single tickets from that far east for some time to come.

      Hope that helps.


  3. Our family of four is flying heading to Maui June 21-28. We’d like to spend a couple of days on Honolulu, which we can add either before or after our week in Maui- we’re flexible. I have been waiting for my husband’s companion fare with Alaska Airlines to hit his account so that I can combine it with my companion fare and basically get tickets at half off. I was not concerned about two weeks ago as flights were looking pretty good nonstop from San Diego/LA to either island. Then his fare hit the account and prices shot up! Right now it’s looking about $900 minimum for nonstop tickets, and not much better for those with 1 or more stops, many of which are redeye flights. I’m also noticing that seats are few and far between…..tough when traveling with two elementary-aged kids. Some flights allow you to get into seat selection and actually have none left without an upgrade charge!

    Do you know if Alaska will add another nonstop flight if the ones listed sell out? I’ve been tracking using a couple of apps and they’re telling me to keep waiting for prices to drop, but when I’m trying to get four seats pretty close together (or 3+1), I’m getting nervous. Do I just bite the bullet?

  4. Hello!

    My family of 4 is planning a Maui (from Denver) vacation mid-October, 2019. Our dates can be somewhat flexible, but prefer to leave Denver anywhere from Oct 10-14. Could you please let me know when would be the best time to buy airfare and what is a reasonable price I should jump on should I see it. Thank you so much!

    1. Hi Hazel

      Right now the price is $686 RT on the nonstop, which isn’t bad considering all the time it will save you. For that suggest buying now as it probably won’t improve.

      On the other hand, prices could drop to the low $500’s with a stop en route. And for that you might need to wait a few months.


  5. Thanks for providing this website as a resource to those heading to Hawaii. My family of 4 is heading from San Diego to Maui in Mid July (Saturday to Saturday trip). I’ve been holding out for Southwest to open direct routes but now I’m starting to question if rates get near or below $600 RT on another carrier if I should book with them instead of Southwest. I know you don’t have a crystal ball, but is it still worth waiting on Southwest? Thanks!

    1. Hi Mike.

      Mid-July is a touch time to bet on a deal. But this year is unusual – oh so unusual. When Southwest gets back to announcements, that route will occur. Of course they’re hoping not to have to discount very much during peak summer travel. Will they? That’s unknown. So long story short – to ease your mind the most, then go ahead and buy now. If you’re flexible and willing to go into the unknown, then wait and you “might” be pleasantly surprised.


    2. Hi,
      I’ve already taken a chance with Southwest and snagged a one-way fare from SLC to HON for $198 on Oct 30. Do you think I have a chance of getting the same price for my return flight on or about Nov 6-9?
      Thank you for your reply!
      Michael B

      1. Hi Michael.

        Looks promising as there are already fares of just over $200 in that market with one stop. Nonstop is sky high.


  6. We also have points on Southwest and are awaiting Kauai. Our dates are a little flexible for July 10-24 from NYC. United and American Airlines have a base fare with no bags and no seat choice of $577. Trying to figure out if we should just book or wait to use our Southwest points. What do you think?

    1. Hi Lisa.

      Those are expensive dates and the fare you quoted is quite reasonable for summer. Southwest has a couple of variables in your case that include flights to Kauai not yet being announced, and the fact that two tickets will be required.


  7. We are traveling from San Diego to Honolulu. Went purchase flights yesterday from Alaskan Airlines for July. So excited price was $259. When I went to purchase, screen refreshed and tickets went up to $339. I was so upset. That unfortunately is not a 40% savings. Any idea if there will be any price breaks again for summer? Thank you!

    1. Hi Lisa.

      Yes fares change up to 5x daily as well as when inventory is depleted. Frustrating when that happens, and we’ve experienced it too.

      Not sure what further deals are ahead, but our take is for continued downward pressure on prices and more opportunities like this. An unusual year to say the least.


  8. I found your website in January and your info/recommendations have been really helpful since this will be our first trip to Maui. My wife and I currently have a June 1 – June 8 hotel booking and it will be tough to change our dates to midweek travel. I’m kicking myself for not booking round trip out of San Diego for $350 a person back in January. I slightly prefer LAX, but I’ve been planning on going out of San Diego with all the SWA hype. Is there any hope for me to get the price tag down from the current $550-600 per person or am I doomed at this point since I’m traveling on a weekend? Any recommendations? Thanks for all your help and keep up the great work!

    1. Hi Matt.

      Thank you. Unfortunately it doesn’t look like is going to improve for your dates, unless Southwest gets on that route by then. That we should know soon enough, so you might as well wait.


  9. Hi there,
    We’ve been waiting and waiting on Southwest for Kauai. Do you think it’ll get any lower than $179 one way from OAK to LIH? Would hate to buy four tickets now and in a couple weeks see Southwest launch $99 one way or something like that!

    Thank you!

    1. Hi Priscilla.

      It all depends on when you are traveling. They may have great fares for April or May, but beyond that prices will rise.


  10. We are traveling to the Big Island in July. We’ve flown the Alaska flights before, but would prefer SWA if possible. Any chance they will match todays Alaska pricing?

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