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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. WOW great prices.
    We live in central Canada, so there is no testing partners as of yet, hopefully soon.
    Thanks for all the information that you provide.
    TW

  2. Hi! I really appreciate these helpful articles and share them with many friends. We have a vacation booked in Kauai the last week in October (this was booked a year ago). We would be flying out of LAX- but it looked like maybe there weren’t going to be any direct flights from Lax to Lih until November on Hawaiian Airlines? (We have flight credits on Hawaiian so we have to use this airline). Do you know if we will be allowed to fly to Honolulu first, then to Lihue? Or would that connection require extra Covid testing…? Thank you for any insights you may have!

    1. Hi Erin.

      We think it will be resolved in the next day or so and there will be no extra testing or quarantine required.

      Aloha.

  3. Thank You for all the good information! Booked Kauai car rental in March & received an email today saying price has gone up $140 due to Advantage closing & they had to rebook me.
    Unfortunately, I think it’s time to just cancel my November trip…
    Too many uncertainties.

    Thanks!

    Julie

  4. Hello Beat of Hawaii,
    Thank you so much for all the helpful and insightful information about your beautiful islands. We’ve had to cancel 2 trips planned to the Big Island and have current reservations for a Nov 2020 trip to Kona. While we are thankful the islands are opening we are concerned about what will be open. For the amount of money spent to get there we do not want to be resort bound only! Will restaurants, tours, shopping and sights be opening? We can always hold off til 2021 depending on Hawaii’s reopening plans. Thank you so much for your articles… I recommend them to everyone we know planning a trip!

    1. Hi Jan.

      Thank you. We can’t say yet what will be open for your November trip to Kona. We’ll know much more in the period between now and October 15, if you can wait. If not, then 2021 should be safer in that regard. And just one more thought. Coming this November could be quite unusual inasmuch as we will not have anything near the normal number of visitors.

      Aloha.

    1. Hi Debra.

      This is available online, so the route you are looking for has either sold out, or you aren’t looking (by month) at the available dates in April and May only.

      Aloha.

  5. Aloha! Hope you guys are doing well. Thanks for the heads up on the $99 Alaska deal – its a great price, but you can’t get a non-stop flight between Oakland and Kahului on Tuesdays in either direction. Do you know why they cancelled their Tuesday non-stops on that route? We had previously booked with them, but switched to Hawaiian when Alaska cancelled their non-stops on Tuesdays (we had to stick with a Tuesday flight because we couldn’t change our lodging reservations). Thankfully, they gave us our full points and $ back.

    Mahalo,

    Debi S

  6. Hi! You guys are awesome. I booked a decent deal through you last week bc I didn’t want to miss my chance to save some money in the peak of summer. These $99 rates are obviously amazing, do you think there’s any chance of them showing up end of July/beg of August? Maybe once Southwest is back in competition? I bought trip insurance just in case!! Thanks for all of your help!!

    1. Hi Tracy.

      Thank you. Yes there’s a chance but probably not end of July and more like second week of August and beyond. So many variables that no one can predict.

      Aloha.

  7. Flights to hawaii PLEASE,
    Need to see kona and big island.maybe kaui VERY VERY much..
    From st.louis lambert airport in Missouri please.
    Need much much lowered fares.
    Thank you so very much!please

    1. Hi Kevin.

      Mid-week fares for spring and fall are just over $600 RT with good connections. Probably won’t improve from there.

      Aloha.

      1. Book RIGHT NOW BROTHA with the $99 fares out of California……then worry about your RT flights to and from home !!!!

  8. Hi,

    Possibly a silly question but I’ve always wondered, what is a “properly packed” box of pineapples? We want to bring back a few but of course don’t want to pay the crazy prices at the airport. We always stop at Costco so that would be ideal, but we’re just really unsure how they should be packaged.
    Thanks for helping out!

    1. Hi Kim.

      Sorry, but we don’t know exactly how that could be interpreted either. Gut says put them in a box that won’t get crushed in the luggage hold and you should be fine. Let us know how it goes.

      Aloha.

  9. Hello,

    I have been checking your site daily for the last 6 months and want to thank you for the consistent updates! We are planning a trip to Kauai and Maui from Boston from 3/6 or 3/7 til 3/20 or 3/21. We got the Hawaiian airlines credit card with the one time companion discount for a round trip flight, so we are planning to book a round trip flight from Boston to Honolulu to get the discount and then buy island flights after. Tickets recently went up a week or two ago, but I have been following your page and it seems that they might have new sales as Southwest gets closer to releasing more flights. Do you think it would be best to buy tickets now or wait for a sale? Also, do you think it is worth it to get the extra comfort seats or stick with main basic.

    Thanks,

    Kay-Lee

    1. Hi Kay-Lee.

      Thank you. Since you are flying on weekends, it doesn’t seem likely that prices will go down. It is going to cost $800+ RT plus interisland. Southwest won’t have any impact on this route. Thus probably no advantage in waiting. Would highly recommend the extra comfort seats from our personal experience. But then it depends on how stressed you get flying. The extra room really seems to help.

      Aloha.

      Aloha.

  10. Aloha:

    I am fortunate to live in the west coast (San Jose) and can take advantage of cheap flights to Oahu, HI. I booked airfare and hotel to Oahu, HI for the first week in March. A relative wants to join in our trip and he is coming from Chicago MDW. I am not familiar what is “good” airfare from Chicago MDW to HNL. Any suggestions, recommendation and tips are appreciated.

    Leyland.

    1. Hi Leyland.

      $600 or so would be a good target for MDW-HNL. Perhaps wait until December to January to book so long as you are doing mid-week travel.

      Aloha.

  11. Hello,
    I have been watching one way flights from Boston to Kona on February 15-16. When I first began searching, I could have gotten a wonderful deal on American for $339 but I wasn’t sure if we were going directly to Kona so I didn’t book it. Now the prices have increased significantly.

    My son is getting married in Kona and has rented a house from 2/18 – 2/25 in Kona. I wanted to fly out a few days earlier to get adjusted to the time difference. We had thought about spending a few days in Honolulu but then realized that it would probably just be best to go directly to Kona.

    I did book my flight home on 2/28 with Hawaiian airlines from Honolulu to Boston and got a decent fair, although they did go down after I booked.

    Can you suggest which airlines would be best to make the long trip out to Kona and also should I expect any drop in fare? I was hoping to have only one stop on the trip with the least amount of flight time/travel as possible.

    Thank you so much for your help and suggestions.

    Linda

    1. Hi Linda.

      The problem is you’re flying on Saturday so that will cost you significantly more. Doubtful it will drop from current mid $500’s one way. If you can go during the week, then the price will be up to $200 less. Take your pick in terms of the airline – they all have good connections and under 15 hour transit times.

      Aloha.

  12. Hello,
    Friends and Family members are planning a trip next year in October 2020, our dates at this time are flexible.
    When would be the best time to start looking for lower rates on air travel for the month we have in mind.

    Thank you for all the information you provide its very helpful.

    Thank you
    Debbie

  13. Aloha,
    I enjoy you insights and flight data. Please advise me the best time and target price for flight from Little Rock, AR to Honolulu from mid December until mid February. My dates are flexible.

    Mahalo nui loa,

    David K

    1. Hi David.

      Mid-December puts you into high season unless you plan to leave by 12/10. It you do leave by then, flying mid-week, then it looks like you’ll pay between $750 (2-stops) and $800+ (1-stop). If you leave later, plan to add at least $100 for the departing flight or more, depending on the day.

      Aloha.

  14. Hi, always appreciate all of your insights. Do you have any advice about the best time to buy tickets from EWR/JFK to Kona May 18-28, 2020? What’s the best fare we could hope for? Thanks so much! Ellen

    1. Hi Ellen.

      Best hope is probably high $500’s. Right now, it is pricing at $755 RT (1-stop) on multiple airlines. If it does drop, that could happen about 90 days before departure.

      Aloha.

  15. Hello –

    Thank you for all of the insightful information! We are looking for round trip tickets from SLC to LIH for 5 people January 9 – 16th, 2020. I’ve been watching ticket prices closely, but they appear to be moving higher ($549 RT, 1-2 stops). Should we buy now or will ticket prices come down between now and then?

    Truly appreciate your help!

    Scott

    1. Hi Scott.

      If you want to get into very long travel times, price might drop to low $400’s. For anything reasonable, cheapest is going to be low $500’s. That is available now in January, but just not for your specific travel dates. There’s nothing to indicate those won’t come down too, but whether they will of course, we don’t know. It doesn’t appear prices will go higher.

      Aloha.

  16. Hi,
    Thank you for all the great information you post. It is so helpful. We are looking for a one way ticket from Maui to SF or SJ in March 2020. This current fare deal only runs to the end of February 2020. Do you think we will see some of those rates in March 2020 anytime soon?

    Your help is greatly appreciated!

    Thank you,
    Trina

    1. Hi Trina.

      Yes. wait for that. First half of March will see reduced prices, but second half may not due to spring break.

      Aloha.

  17. Aloha,
    I have been following your great blog for a couple of years and love it. I have never been able to find any of the flash sales occasionally listed such as the latest. I try to locate the $159 Alaska Airline fare from Sacramento to Maui by going to Alaska Air’s site but the lowest is $189. When I click the Alaska Airlines link on your site, it takes me to Expedia and the flights are even higher. What am I doing wrong? Mahalo for your otherwise very informative site and patience with some of us mainlanders.

    1. Hi Gary

      Thanks. Not sure what dates you are looking for. That offer is still there with some dates in every month. You do need to use a flexible date/calendar search since it is a bit a majority of days each month. And only mid week.

      Aloha.

  18. Hi there. We’re looking for May 2020 fights, SEA-OGG, leaving 5/23,returning 5/31. Prices on Hawaiian today are $578, but Alaska is $798. Are Alaska flights expected to come down to compete?

  19. Hi,
    Just fouund your site and trying to take it all in. Hoping to pull togheter a family trip for 4 (possibly 5) adults in the first two weeks of January 2020 (say 1/2 – 18). Would like to visit several of the islands (maybe 3) as it might be the only chance. Trying to decide on which–we like nature (National/State Parks) more than resorts, but do want to see Pearl Harbor site. We would fly from/back to Portland, OR. Priced multiple one-ways (PDX – HNL, HNL – OGG, OGG – ITO, KOA-PDX for $802 apiece–is this good? the best for January? It was on Hawaiian Airlines. Is there a better route order/combination? Thanks so much for your input.

    1. Hi Beverly

      We’ll address trans Pacific only, as inter island is a separate issue and pricing is related largely to time of day and day of week choices.

      We are seeing airfares of just over $600 for your routes and dates. It might be better to transit via Maui and Honolulu for best prices and options. If dates are set, price may not improve. If flexible, for mid week travel, and starting a week later, improvement of up to $150 by waiting is possible.

      Aloha.

  20. Hello there!

    Before I ask my question, let me just say I love your site and it has been super informative! Thank you!

    Ok, can I ask please, from the East Coast (mainly EWR or JFK), we’d like to fly direct into Maui. Connections through other airports or islands is ok too..when is the best time to buy tickets for February travel?
    Any suggestions on airlines or connecting Flights? It’s seems there are a lot more options from the west coast, so I appreciate your thoughts.

    Family of 4 all adult tickets.

    Mahalo!

    April

    1. Hi April.

      Thank you! Price target is $550 and currently there are $580 fares with a quick connection on Hawaiian. So if dates work, might be worth buying now. Getting all the way to Hawaii on one flight seems to reduce chances of connection problems, in our experience.

      Aloha.

  21. Please help me! I am searching for the deals on Alaska & Hawaiian and they are not coming up $149 each way. We are flying from LAX to Kona in February returning in March. Is there a code I need or something?

    Thank you.

    1. Hi Lynn.

      Not sure why you thought there were $149 fares on that specific route, as that was not what we indicated.

      Currently priced mid-week from $550 RT but could drop to about $400. That might occur sometime between late summer and fall.

      Aloha.

  22. Aloha!

    Can you please tell me when is best time to buy tickets from LAX to OGG June 7 and return June 23, 2020. It’s for a family of 5. My preferred airlines is Hawaiian or Alaska. Not sure if to wait and is it better to buy one way tickets as I see deals. I’m a little concerned with Hawaiian Airlines moving terminals and what that means to our airfare price and accessibility to get through terminal. Greatly appreciate your advice and guidance.

    Mahalo!

    Elsie

    1. Hi Elsie.

      Because your outbound is at end of low season, and a weekend, it would be best to treat entire trip as high season. Therefore, best suggestion is to buy as soon as it is available. Target price is in low $600’s, which if you can get it, would be great. Southwest could be a factor in lowering prices later, but that is definitely not guaranteed. Let us know how it works out.

      Aloha.

    1. Hi Colleen.

      If entire trip isn’t completed within first week of June, then in range of $750-$1,000 RT.

      Aloha.

  23. Hi! Four of us plan travel from Sacramento to Maui on Thursday, December 5. Then Kahalui to Lihue on Saturday, December 14. Return to Sacramento on Sunday, December 22. We’d like to use Southwest credits, if they will be serving Maui by then. Otherwise, what would be our best options and when should we purchase our tickets? Thank you so much! Sharon W.

    1. Hi Sharon.

      Do not wait on Southwest if you are determined to go, as it is highly unlikely. You are flying largely in high season, especially the return segment. It would be best to buy all segments now, with the inter-island and return being essential. The outbound has more flexibility being mid-week and low season. Hope that helps.

      Aloha.

  24. Thanks so much for the great site and information! We need to book a roundtrip from Maui to Kauai in late October. I’m finding RTs at about $800-$1000. Any ideas if this will drop or if I should just go ahead and book it now? Thanks very much!

    1. Hi Lisa.

      You are indicating Maui to Kauai at $800+ which it appears isn’t what you are intending as your route. Please let us know where you are flying from/to.

      Aloha.

  25. How come the good deals are always west coast? Let’s start having good deals out of Chicago and Milwaukee. If there’s any area that could use a break to Hawaii it’s that area. Thanks

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

  27. 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.

  28. 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.

  29. 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.

  30. 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!

  31. 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.

  32. 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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