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$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. If you are smart, you will NEVER fly Southwest anywhere. I can tell you all about how shoddy their maintenance practices are.

  2. Great site guys! Looking to travel to Maui from LAX anytime in October 2019 for 6-8 nights. Is $360 RT about as good as I’m likely to see? Are the days of $199 RTs from the west coast long gone?

    1. Hi Steve.

      Wouldn’t put it that way – long gone. Just not right now. Anytime you can get RT to Hawaii in the $300’s you’re getting a great deal.

      Aloha.

  3. Hi, we are traveling to Maui next year in March. We are flying from St. Louis to San Diego (I will worry about that flight later). What I would like to get your input on an Alaskan Airline flight price, San Diego to Maui (first class) then a week later Maui to San Diego (main cabin). I’m splurging on the flight there because it is our 30th Wedding anniversary. We would be leaving on Saturday both ways. Please let me know you thoughts on a price of $1,670. Thank you.

    1. Hi Kimberly.

      It largely depends on dates. When checking 3/14-3/21 just now (both Saturdays), round trip first class is $1,286. That’s a fair price. Actually we don’t find any airfares as high are you are showing, and having one way be in economy, would be even less.

      Aloha.

  4. Aloha,

    Thank you for this awesome blog. My wife and I are planning on going to Kauai December 14th through 19th. We have a ton of points on southwest and would prefer to connect through Honolulu to Lihue. Do you think that connection will be running by then with southwest?

    We are coming from Dallas so we may need to go with another airline. In that case when do you recommend booking?

    Thank you so much for your advice!

    1. Hi Brad.

      Seems likely they will be flying here by fall so you should be good on that aspect. You are flying too late in December to have good pricing. You’re also flying on a Saturday. Not certain this is going to play out to your liking and waiting won’t improve the deal.

      Aloha.

  5. For over a year, 6 families planned our reunion in Honolulu from August 3-11. The Southwest Airlines announcement to Hawaii looked promising. But that over-hyped Southwest Airlines sale in March 2019 failed us. Only two families got their flight reservations (one from OAK to HNL via Alaska; the other family coming from Washington DC via United). The Southwest Airlines sale in March (from OAK, SFO, and SAN) sold out so fast and that lack of inventory left 4 families with nothing but $600-$700 Hawaiian Airline flights. Every day we look for flights online makes us all feel like backing out on our vacation as it becomes more and more unaffordable. We all have our hotel reservations locked in Waikiki, but 27 of us have no way to get there. Question: Will Southwest Airlines or ANY other airline open flight inventory before June 11th. That’s our target date that will either make or break our family reunion.

    1. Arlene,
      Southwest really threw a wrench into this years pricing.
      • First they announced they would be flying to Hawaii….so the competition waited until they could gauge the SWA pricing. The SWA one day sale did not provoke any reactions with its limited selections…if anything it drove prices higher.
      • Then the government shutdown delayed the SWA Hawaii approval…and when they did get approval and announce the sale it was really a silly sale that lasted a few hours with very limited selection from Oakland and San Jose.
      • Then SWA announced that future sites and sale would be announced in April…then May (Sacramento, San Diego, LAX)…that started the competition price wait cycle all over again.
      • Now throw in the Boeing 737MAX mess…on the surface SWA stated they will not be impacted since the MAX to Hawaii… everyone celebrated right…..WRONG!
      In reality, SWA removed their 40 737MAX planes out of service and is now using the planes intended for Hawaii for the MAX routes. They recently announced this will delay the next Hawaii routes and sale….until when?…WHO KNOWS!
      So everyone from passengers to the competition is still waiting for the next SWA announcements.

      With June a couple of days away….I don’t expect to see any sales or flight additions for June and July….its the high peak summer season.

      Sorry to say that East coast flyers to Hawaii will have to pay the crazy high prices if flying in June or July.

    2. August is peak season. Last summer we paid $900/each for tix from Seattle to Hawaii. Those prices of $600-$700 flights don’t sound that bad!

    3. you seem to imply that there are no inventory seats available to Hawaii … which is not the case. you are seeking cheap fares during a time of the year that is really expensive. it seems that southwest should not be blamed for your misfortunes. can you realize that the “over-hyped” southwest fares to Hawaii is your viewpoint that is negative in nature ,,, since you and your tribe people were not able to secure the low fares that alot of other people obtained … like me … ALOHA! HAWAII >>> See you soon!

  6. Hello
    Thank you for all the great information. The minute I received your email I clicked on the route I wanted. I am looking for August dates from Oakland, CA or nearby airport to Honolulu. Unfortunately I didn’t find the prices you had mentioned. The San Jose to Honolulu route took me to Expedia booking and it was in the $600 round trip. I also went to the Airline direct website and same thing. Should I have looked somewhere else for the deals? Also what are the chances of southwest announcing Sacramento route before August please?
    Thanks you!

    1. Hi Monila.

      The next time you have an issue, please leave us a comment write away with what you are looking for and we will try to help. The day after doesn’t work.

      Chances of Southwest announcing SMF before August are slim.

      Aloha.

  7. Hi, We are looking for 1 way flights from San Diego to Honlulu on Oct. 13. The prices have dropped to $283. Is this a good price or should we wait. Thank you so much for your reply.

    1. Hi Rae.

      If Southwest gets going by then it won’t be considered a good price. If they don’t, it will. So it is impossible to predict, as their starting date is based on the Max returning to flight and no one knows when that will be.

      Aloha.

      1. Hello, thank you for all the great info. My question is I am flying from Louisville KY. to Hilo, return is Kona to Louisville. Travel dates are highest of high season, Dec 14 -Jan 01, is there a way to include both Big Island Destinations or should I book each trip as a 1 way? I have around 3,000 to spend . Doable?

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