The Best Hawaii Deals Ever Among 2020 Predictions

With the end of 2019 just days away, we’re looking back on 2019 while offering updated predictions for 2020, and the best Hawaii deals ever.

2019 Hawaii Deals in Review.

This will be remembered as the year of $99 airfares. In actuality that started late in 2018, when there were two brief rounds of $99 airfares launched by Alaska and United. Then in 2019, it resumed in earnest, with $49, $79 and $99 airfares when Southwest Hawaii flights were first announced this past spring. Within minutes, the $49’s were gone, and within less than 24 hours, that sale was over. The $99 Southwest Hawaii airfares returned one more time last spring. Then last week, there were $77 airfares, courtesy of a one day Alaska Airlines Hawaii sale. Flash sales as they are called, have become common from both Hawaiian Airlines and Alaska Airlines.

1. Max fleet return to service delay complicates competition and slows some Hawaii Deals.

Southwest Airlines finally arrived in Hawaiian Airlines territory this year. This has been so long awaited as to be agonizing for everyone. The competition that we had expected to begin early in 2019, was largely delayed. That was due mostly to the removal from service of Southwest’s Boeing Max 8 planes, that are their planned workhorse for future Hawaii flights and expansion. Southwest then shifted plans multiple times, and in the end, announced more Hawaii flights using the existing 737-800 fleet. That announcement came in order to continue, albeit more slowly, their necessary Hawaii expansion momentum.

It may be another six months or so until we see the Max planes in the skies of Hawaii, and with them will come new routes and even more deals.

2. Best Hawaii travel deals yet and when to buy.

All indications are for 2020 to be the strongest Hawaii travel year with the lowest overall prices ever seen. There will be fierce, intermittent fare wars between all airlines serving Hawaii. Those will resume at any time.

In order to take advantage of upcoming fare wars, less advance planning than normal may be possible, even for summer and holidays. To score the very best money saving deals, you will need to be flexible and at times, relatively last minute. Case in point is last week’s $77+ sale, which was only valid in January and February.

Also try to make plans for mid-week flights whenever possible. Virtually all of last week’s $77+ airfares were for mid-week travel only. The airlines will try (but may not succeed) in keeping more valuable weekend fares away from ground floor pricing.

3. All time low Hawaii airfares from six airlines.

Winter, spring, summer and fall 2020 should all feature on-again, off-again, exceptional sale prices from all airlines serving Hawaii. Even regular non-sale prices will be kept significantly lower than normal. Airlines participating in the competition include Alaska, American, Delta, Hawaiian, Southwest and United. No one will be left out. Hawaii is important to each of the airlines for varying reasons. Hawaiian, with the biggest stake in the game, will have the most important moves to watch. Alaska has a huge number of flights to and from Hawaii as well, and they will be the second ones to watch. Alaska cancelled its San Francisco and Sacramento to Kona flights starting next March. There could be a further shift in Alaska’s Hawaii strategy in 2020 that would reduce Bay Area and San Diego to Hawaii flights. This is due to competition from Southwest.

4. Low season 2020 Hawaii price predictions.

From the west coast, expect to see best low season sale prices starting at under $200 round-trip, depending on the market. When traveling from the mid-west and east coast, you’ll pay $250+ more on average.

5. High season 2020 Hawaii price predictions.

Peak Hawaii travel periods are in effect during Spring Break (late March to mid April), from mid-June through mid-August, and at Thanksgiving and end of year holidays.

During the high season, look for west coast sale prices to start at about double off season pricing, or from under $400, depending on the market. When traveling from the mid-west and east coast, again expect to pay $250+ more on average.

6. Our top picks for the best Hawaii deal gateway cities.

San Diego, San Francisco, Oakland, Sacramento, and San Jose will feature the most frequent and best priced Hawaii deals, and to a slightly lesser degree, Los Angeles and the Pacific Northwest. Once additional expansion of Southwest’s Hawaii flights occurs, watch for competition fueled Hawaii deals to spread further afield, possibly including Phoenix, Las Vegas and more. Those could come online starting in the 2nd half of 2020 and after.

7. Best ever inter-island airfares too.

As we have already seen, we’ll have intermittent airfare sales for island-hopping starting at about $30. Even regular fares will come down to $50 or more each way in most markets. These represent dramatic savings and prices that hearken back two decades and more. That as a result of competition between bellwether Hawaiian Airlines and Southwest Airlines.

We welcome your thoughts and questions.

Updated 12/26/19.

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

  1. Looking to fly DEN-LIH in July (7th-19th). Would love nonstop but they are at 1020 right now. Flights with stops are less, but not by much. Trends for this route? Debating jumping or waiting. thanks!

  2. Looking at roundtrip flights to maui from oakland or sacramento oct23-nov 6, 2020. Lowest price Flights are $164 each way. Any thoughts on if there will be lower prices, of if we need to choose these?

  3. Flying from Austin to Maui 7/11-7/18. What would be a good price point to book at? We have never flown to HI before so we don’t know what’s a good deal. We are seeing $786 rt with a stop in LAX. Also when should we buy? I’m very trigger happy right now because I just don’t want prices to rise!

  4. Hi I was just wondering if you have good prices for shuttle s from and to HI airports? I enjoy your articles. Thank you for being online with
    All of your recommendations and suggestions.

    1. Hi Marilyn.

      Thanks for all of your comments! We don’t use the shuttles so can’t say the cost from personal experience. Uber is very reasonable to and from HNL and we’ve done that a lot. Seems to save nearly half off cab fare.


  5. When would be the best time to purchase ticket for Kauai leaving LAX from July 9-14th for 6 people.It seems high at this time,what would be the cheapest airfare it can go.When will be the best time to buy or best to wait?thank you very much.Appreciate any input you can give

    1. Hi Essie.

      High compared with what? Starting at $418 RT nonstop, that is about $300 less than normal for that time of year. Suggest buying now.


  6. We have a place booked for a year from feb 11-21st but prices havent dropped below 750 the entire time, for Hawaiian, will they ever?

  7. Looking to book from North Carolina to either Maui or Oahu. Dates are very flexible (month or day of week). Looking to spend about 10 days anytime after June 8th through August 11th. Need a deal. 4 RT tickets. Prefer in and out of RDU but CLT OK. Layover on West Coast (even for a few days) is ok.

  8. Hi! We are planning to fly from Chicago to Maui the end of March/first of April … do you know if there will be any good deals coming up? We are also hoping to do a day trip to Honolulu at some point during our trip. I’ve just been made aware of your site so I’m excited to have you as a resource! Thanks so much for taking the time to do this! -Stephanie

    1. Hi Stephanie.

      First week of April is peak of spring break so don’t expect prices to go any lower and availability could also be an issue for air, car and activities.


  9. Good day,
    I was wondering if there will be sales on or about October/November in 2020? I would be traveling from the New York area. Or would most of the deals be from the West coast?
    Thank you so much for your great help!
    Joe M.

    1. Hi Joe.

      Yes definitely look for reduced pricing, which might occur about three months in advance. If you’re planning for mid-week and not near Thanksgiving that is. Expect just under $600 RT.


  10. Aloha, I will be in Honolulu from February 1 through February 8. The Super Bowl is Sunday, February 3rd i’m looking for a good place to watch the Super Bowl I was wondering if they have all inclusive parties at some of the bars in the local area? I found one bar at the International marketplace but they’re all sold out. Any help would be greatly appreciated. Thank you. Rich M.,

  11. What would you advise for a group leaving Salt Lake City? What months and which island would you advise is the most affordable?

  12. Hello,

    Is a round trip from LAX to Maui OGG mid-week in September for $388 (main cabin) good price? It’s a departing morning flight (perfect) and returning afternoon flight (good time). Both non-stop.

  13. Our party of 7 will be traveling to Honolulu from Tallahassee, FL 3/21 and returning 3/28. Would you please advise the best time to purchase less expensive tickets for our trip? I appreciate all the information and tips you have provided on getting to Hawaii and having a great trip. Thank you!

    1. Hi Lynda.

      Currently almost $1200 with quick one stop connection. Best price might be $1000 if you wait, but likelihood of that happening isn’t great. Reasons are you are flying Saturdays and your return is during spring break.


  14. Looking at 5/30-6/7 from Dallas to Honolulu. United is about $709 round trip with a short layover in San Francisco. Should I book now or wait and see if it drops?

  15. Please if you have any idea of when Southwest will open their schedule to Maui through st least mid April would be much appreciated as I’m trying to get friends to join me flying from San Jose to Maui March 28th thru April 4 utilizing my miles. I can book them on American now from Detroit to San Jose. Thank you I’m an avid reader.

    1. Hi Jerry.

      Their September 26 release is for flights through April 15. We don’t know the date for the following release but would guess maybe end of October.


  16. Aloha,
    We are travelling to Maui from San Francisco Feb 4/2020 and I found a one way Non stop for $159.00 on Hawaiian airlines. Would it be recommended to book now? We will be coming home Feb 26 from Honolulu but it looks cheaper to book one way tickets versus multi city. Does this make sense?
    Thank you I really enjoy your posts and am learning slot about Hawaii from them.

    1. Hi Jane.

      Good price on that first route. Wouldn’t hesitate. On the return the price should come down about $80 or so if you wait on that.


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