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.