72 thoughts on “The Best Hawaii Deals Ever Among 2020 Predictions”

  1. can you tell me a good time to purchase tickets from miami or ft lauderdale to kona for end of may early june when kids get out from school. only one stop I can do. senior citizen disabled. been using united and they have been wonderful. will southwest be up by then. use to fly them all the time when I lived in denver.

  2. Hello! I’m curious if you’ve continued with Opinions Take Flight. I found your post from 2017 and it would be interesting to hear if anyone stuck with it and if so, how many miles they got. I just started taking surveys yesterday. Minus the 350 point sign on bonus I’ve made 163. It seems like a lot of work for very little. Thanks! Erin

  3. Please advise me what pricing to expect on planned trip fro LIT to HNL from early January until early March 2020. Mahalo

    1. Hi David.

      For any kind of reasonable duration 1-stop connection, it will cost about $750 RT mid-week. If you get into 2 or 3 connections and very long layovers, price could go to low $600’s.

      Aloha.

  4. Planning on mid September 2020 trip from Pittsburgh to hnl. Will not fly coach, comfort plus probably”. Would you recommend waiting for sales or booking early?

  5. Hi,
    I’m hoping to work out a first timers-family trip (4 adults) to several islands. One grown daughter lives in Portland; so the group departure would be from PDX or SEA probably to HNL to start off unless it makes sense to get a connection down to CA for heading out? Have in mind RT departures from and back to the mainland around January 6-January 20/22 thereabouts (2 weeks+). Think any fare changes for that time frame from Pacific NW will happen at this point or is it too early in Jan. for something to change with last week’s changes? Any recommendations as to the order of the following 4 islands to go in (3-4 days each): Kauai, Oahu, Maui, and Hawaii?
    Thanks so much! Bev

    1. Hi Bev.

      The order of islands probably won’t matter much in terms of convenience or cost. But for trans-Pacific, generally Maui and Oahu are easier, more frequent and sometimes better priced. Not always. Both PDX and SEA have Hawaiian nonstops in that market in the low to mid $400’s into one island, and out of the other. Not bad pricing. Might improve some, but not very likely.

  6. Aloha! Mahalo for the hot tip – we scored 2 inter-island r/t tix, O’ahu to Kona for $58 each! A little over a year ago we paid $185 each!

    Several of us are traveling to Kauai in early February 2020 – I’ve got my ear so far to the ground I can hear footsteps!

    Mahalo again (and again!),
    tea

  7. Hi y’all,
    Were looking to fly from mco to ogg in mid March 2020 till first week in April.
    What should we expect for airfares & when to purchase.
    Many thanks for your assistance.
    Richard

    1. Hi Richard.

      Spring break. There are $713 RT airfares, 1-stop with fast connection on multiple airlines. Wouldn’t wait on those. Great price for spring break.

      Aloha.

  8. Aloha! I enjoy reading your articles and always appreciate the travel tips and insight.

    When should I look to purchase flights from IAH to OGG for May 2020 at the best price? Mahalo!

    1. Hi Liz.

      Thanks. So it looks like there could be lowest fares of just over $500. Not available yet and that could happen (if it does) at any point honestly). Those best priced fares will be with 2 stops and a slightly longer duration (not a huge layover though).

      Otherwise it is going to be in $700’s with 1 stop. That’s available now if you’d prefer.

      Aloha.

      1. Hello and thank you so much for all the information that you post here. Very helpful. When do you foresee there being deals from Phoenix to Maui? Would like to go in end of May but not sure how long I should wait to book and what you think the best round trip fare I can expect would be. Prefer nonstop.
        Thank you in advance.

        1. Hi Francine.

          Little competition at this point, so expect to pay just under $500 RT, mid-week. Not likely to improve, so suggest buying now.

          Aloha.

        2. Amen; I’ve been monitoring the flights in the hopes of getting a deal for my mom to come visit. Thanks, Beat of Hawaii, for keeping us posted!

  9. Aloha, I’m trying to bring 2 kids home to HNL from STL for winter break on 12/14. Costs seem unusually high. Is there a time frame I should be looking at when booking? Trying to do it without putting them through 21-24 hour travel times.

    1. Hi Tracy.

      You didn’t say return date. There is a $700 fare on American with quick stop is very reasonable but again depends on return. Waiting isn’t going to improve your situation. Just saying.

      Aloha.

  10. Can you please tell me, if I’m taking off to Oahu May 19th, should I wait till closer to May to book or should I book as soon as Southwest opens May? Thank you for your guidance.

    1. Hi Flo.

      It is hard to know just how the competition will work for next year, so there is no clear answer as to when to buy. It is more about having a realistic target price in mind for your route and dates. Sales will be on again, off again. You also didn’t mention where you are flying from.

      Aloha.

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