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

  1. Aloha! We are looking into visiting Kauai in summer 2020 (June). I found RT from Oakland on Hawaiian for $567 so far. Do you think that may go down? When do you suggest the best time to purchase air would be?
    Mahalo!

    1. Hi Jo.

      Yes we think it will go down. As indicated, summer prices have potential to be in the $400 range. You’ll have to just wait and watch with us if the best possible price is your objective.

      Aloha.

  2. Hi Nick, when did the flight times change? For years we have been going from OGG at 11:35 to SJC on Hawaiian landing at 7:30pm. During September the flight schedule changes leaving OGG at 2:40pm landing at 10:35pm. Too late to drive to our destination comfortably.
    Mahalo,
    Janet C

  3. Hello
    Looking to Fly from Chicago to Lihue 1/7/20 returning 1/15/20. While fares are cheaper now than they’ve been in months ($520 RT), total duration at the cheapest prices is 30+ hrs. each way! Do you anticipate cheaper fares with shorter flights or is now a good time to buy?
    Love the site!
    Thanks!
    Peter B.

    1. Hi Peter.

      Thank you. There’s a $625 RT on Alaska, with just a one hr connection outbound and just under four hrs on return. It’s actually well priced for that market, if it works for you. Otherwise, competition and prices aren’t looking very favorable.

      Aloha.

  4. We are flying from Vegas to Maui the last week of February. SW will not be flying yet. Do you think fares will go down or should we just book now? I was hoping for the fare wars. Thank you.

    1. Hi Linda.

      Currently $355 on everyone except HA with 1-stop and good connection. Great price. Almost double on the nonstop and not sure that will improve.

      Aloha.

      1. Appreciate all the updated information you provide. Yours is a great site!
        Am looking ahead to a flight from Honolulu to MSP late Jan, 2020,1 way on Delta, non stop. Currently ticket is $673., while skymiles points are 28,500. The points are attractive.
        Could you please comment on the chances of that one way , non stop flight ticket price going down? The price was under $500., middle of June.
        Thanks.

        1. Hi Ron.

          Thanks! With points valued at 1 cent each, that’s indeed a good price if you can get it. Cash cost could come down to just over $500 again, mid-week, if you wait.

          Aloha.

          1. Thanks for your prompt reply, got the 1 way non stop from Honolulu to MSP for the 28,500 skymiles points.
            Part of our group on this trip is flying from Seattle to Honolulu on Hawaiian Air , wondering if you could please comment on if the current price of nonstop round trip ticket of 478.00 might go down before the Jan 2020 trip, or if should book now?

            Great job informing us of the $29.00 flights between the islands.
            Thanks

          2. Hi Ron.

            Competition is rather dormant on that route for the moment. So low to mid $400’s might be about it.

            Aloha

  5. My family is coming to Oahu from Southern CA end of February 2020. Would it be worth the drive to San Diego vs. flying out of LAX or John Wayne? Should they wait for Southwest?

  6. Thanks for your blog and insight. I have a large family group looking to travel in late January to early February. Does it make sense to wait some time to book flights? We live in Idaho, so we have to travel to bigger cities to get the flights like SLC and Boise Idaho. The cheaper flights are out of California, but we would still have to fly to California to take advantage of them, so I’m sure the $99 flights are out of the question. Any expert insight on this? Thanks!

    1. Hi Jamie.

      On just checking, there are $351 fares on United late January/early February from Boise. Quick connection and reasonable price. Not sure it would improve by waiting. Not sure if that works for you, but if so, suggest buying. SLC starting at about $90 more.

      Aloha.

    1. Hi Nick.

      Perhaps starting in next couple of months, or even later. With one-stop should come in just under $500 or nonstop at about $200 more.

      Aloha.

  7. Not sure where these amazing 2019 prices are coming from, but from the Nortwest, in particular SEA and YVR the prices are NUTS this year in comparison to the last three. Traditionally 2 people could fly from SEA/BLI/YVR to OGG for a little more than US$800 for late November – this year, it’s been hard to find any rate lower than US$1200 for the trip (with an Alaska companion fare!).

    Thank God for points this year

    1. I agree with John, the Seattle to OGG fares are the highest I’ve ever seen. Not sure why we keep hearing about low prices. We are thinking seriously about canceling our Feb 15-22 trip with family because we can’t find fares under 1200 per person on Alaska Air or Hawaiian. Any ones that are in the 500-800 range are 18 hrs or longer. When you’ve got school-age kids and parents who work in the school district, the mid-winter break timing can’t be helped, so no mid-week travel for most of us.

      It would be nice to know if we should continue to hold out for a lower price or cancel all our accommodations and go somewhere else this year. Very frustrating.

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