Southwest Hawaii

$99 Southwest Hawaii in 2021 + United Hawaii Expansion Plans

First, starting next summer, United Hawaii service will see new routes to both Maui and Kona. Second, we’ve just seen signs of what to expect next year in terms of Hawaii airfare prices. Read on for details.

United Hawaii new routes.

The airline is doubling down on Hawaii and announced it will fly nonstop four times each week between Chicago and Kona. They are also adding four times weekly service between Newark and Maui.

Chicago has long had ridiculously high Hawaii airfares that commenters have frequently noted. For example, Peggy B. said, “I am always seriously disappointed that none of the best airfare deals ever include Chicago… After 20 years of flying to Hawaii, we are ready to give it up due to always expensive flights out of Chicago.”

Beat of Hawaii: We think Hawaiian Airlines also has an interest in flying between Hawaii and the midwest, perhaps Chicago, although that may be curtailed due to ongoing uncertainty.  

“Now is the right time to take a bold step in evolving our global network to help our customers reconnect with friends, family and colleagues around the world. These new nonstop routes provide shorter travel times and convenient one-stop connections from across the United States, demonstrating United’s continued innovative and forward-looking approach to rebuilding our network to meet the travel needs of our customers.” — Patrick Quayle, UAL VP.

$99 Southwest Hawaii 2021 Pricepoint Set.

There were indications this week of just prices we can expect to see when Hawaii opens to tourism without the mandatory quarantine. Earlier this week, Southwest had a sale for flights through March, and the price at that time was $99 each way. As of today, those prices have gone back up to $129. But the point is that Southeast believes that $99 is the price that will be needed to drive the return of Hawaii travel. We think they are right, and that we’ll see those fares, and even lower ones, from Alaska, Hawaiian, and Southwest. Get ready for that.

The routes that were on sale earlier this week (although they are no longer available) included San Jose/Honolulu, San Jose/Kauai, Oakland/Kona, and San Diego/Honolulu. That having been said, the sub-$100 fares upcoming will be across most if not all west coast to Hawaii routes when things get started.

Will perhaps the lowest airfares ever entice your return to Hawaii?

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60 thoughts on “$99 Southwest Hawaii in 2021 + United Hawaii Expansion Plans”

  1. Can’t wait for nonstop and low fares from
    chicago! We have had so many unfortunate delays in flying to and from Hawaii due to stop overs in CA. Hopefully the Coronovirus will be over so we can vacation again.

  2. I checked Southwest for dates I wanted in March 2021 and didn’t see any low fares youre talking about. I would like to travel the week of March 15th 2021 and be there for 7 days. Any advice on how to obtain those low fare? Looking forv2 people.

  3. I’m wondering if my plans to travel to Maui will still be possible in late October? I’ve canceled it once in April, but I’m trying to be optimistic! Please stay safe everyone!! Is there anyone I should contact? I miss my islands so much! Aloha and Mahalo! A hui hou!

  4. Thank you Southwest. You’re the best and a role model for other airlines .
    We ❤️❤️ You very much+++++

    1. Hi Andy.

      At this point, all bets are off the table on new routes. It certainly was their intention at one point, but that was before the world changed.

      Aloha.

  5. Talk about mixed signals. United announced today that it would be laying off 15,000 employs come Oct 1st, if it didn’t get additional government funding. Also, keeping up with Lt governor Green who is now sick covid.
    Aloha Guys.

  6. The point was brought up about $99 fares being unsustainable and it’s a good one…..like any new entrant to a market
    SWA is going to try and get a foothold in it by money losing fares for some seats. It’s not altruistic, it’s an attempt to expand.
    Double edge sword, for the time being Hawaii needs tourism to return ASAP. But……Hawaii cannot support a tourist market that is based on volume as the number one driver. It simply can’t support unfettered growth and if SWA wants to expand to the point of over capacity
    and high volume cheap seats they may not be all that well received here. Hawaii is currently wrestling with how to manage the return of tourism and the long term view of quality over quantity is a very popular one here right now.

    1. looking for flights ✈️ from Sacramento to Maui round trip. It’s been so long. Two years ago my husband passed and Maui was our favorite place.
      I am now 77yrs old and feel a need to be there again.
      Thanks n many blessings

  7. The advantage of flying with SW is that you can cancel or change a reservation at no cost anytime. I follow my reservations weekly for a price change. We are about to cancel our Maui for October and rebook for early next year.

    1. Actually that’s no longer an advantage….all airlines allow it now and it’s safe to say you’ll be able to getting matching fares
      on Hawaiian and still enjoy their service.

  8. As much as I love Hawaii I would have to pass even if the flight was free! The current situation is not good in Hawaii! I can’t afford to go with the current Covid rules. Anyone that comes to Hawaii right now has to quarantined for two weeks. You can’t leave your hotel room or home. If you do it’s a jail or (I believe the amt is correct) $1,000.00 fine.
    At this moment most stores are closed. The government has been moving back and forth on Covid rules. They are back to Phase 1, you can go on the beach, you have to be in the water. You can’t sit on the beach. That is if you can get on the beach! Public parking is closed. Only places that sell food and essential places are open.
    I follow several people that live in Hawaii on social media, because I love the photos and Hawaii in general. That was the latest from someone I follow.

  9. Aloha Rob & Jeff.
    Hope you and everyone on the Islands are safe and well.
    I read your recent posts and am delighted to hear that there is a prospect of travel returning soon. Safely, I hope.
    I realise most of Hawai’i visitors are from the U.S., but I’m interested to know about the prospect of international visitors being allowed to return. Like many others, I have my ‘bit’ of Hawai’i invested in some timeshare weeks. We are all going to find Maintenace Bills in the not too distant future, but if we can’t get to the Islands, I wonder how we’ll feel or indeed what we’ll do.
    Does there seem to be any light at the end of the tunnel to welcome not just U.S.citizens, but the rest of us?
    Mahalo for all your help and indeed the thoughts of all your readers.

    1. Hi Michael.

      Thank you. Yes, international will be addressed. It must be. We honestly have not heard much beyond the “bubbles” concepts that were floated at one point.

      Aloha.

    1. We are still under mandatory quarantine for incoming travelers from both the mainland and inter island. We haven’t seen any sign of that changing anytime soon.

  10. These would be awesome fares, but for those that paid substantially more prior to Covid and took waivers due to cancelled flights, it seems a bit unfair. I understand wanting to get Hawaii jump started again, but people that are wanting to go will pay normal summer fares. The islands is what brings people.

  11. I think they are on the right track, we have been doing some trial bookings for lodging on Maui for March 2021, and they are currently sky high compared to where we stayed in march 2020. I think both air and lodging will have to make it attractive to travel to Hawaii once it opens up.
    Mahalo for keeping us all informed.
    Aloha
    Bill

  12. Hello,
    I am just waiting for the quarantine to be lifted and I will book and be there. None of this has deterred me from wanting to be in Hawaii! Have a great day!

  13. Aloha, I have HA vouchers worth more than under $100 fare – what happens next? Refund? Another voucher? Forget about it
    Mahalo

    1. Hi Marilyn.

      What are the terms printed on the vouchers? That might tell you how they will be applied. We suspect you won’t be able to apply them for further credit, but do let us know.

      Aloha.

  14. Price is currently not a Concern,Since our tickets are already Paid for. Its the availability of access to the 72 hour before Flight test that Concerns Us.What Lab, Pharmacy is going to be able to Offer that?

    Mahalo,

    1. Hi Deb.

      We’ll have to wait and see what the state says about their three pharmacy arrangements for testing.

      Aloha.

  15. We will not return to Hawaii until masks, social distancing, testing, and quarantining are no longer in our daily vocabulary. For the amount of planning and the cost and time spent travelling to/from Hawaii, I expect to have a real vacation, not one where our movements and activities are potentially monitored or dictated. If we don’t see that happen for possibly years, so be it – we’re perfectly happy doing the staycation thing…and we’ll be saving lots of money in the process.

    1. Aloha. Amen Jackie C. I will include NO vaccine. It takes 4 to 5 years to certify a vaccine and only one percent make it; Big Pharma and Big Government expect a vaccine in 6 months. Right. It probably takes 4 years to certify a new dog food…
      PS: $99 per seat will not pay the fuel across the Pacific. You need to care about that.
      Mahalo

  16. If SWA does $99 one way from Sacramento they better have a LOT Of planes ready to go! I think there are many in California that are just waiting until the Virus is deemed at least on a steep downturn,we’ve made it and turned the corner for sure and the Islands are opening up again and welcoming visitors without restrictions.

    Waiting for it all to fall in place to get back to the Island Love!

    Mahalo and great job on your site, keeping people informed!

    P.S as the old Mervyn’s ads used to say…. Open….Open…..Open…..

    1. We are right there with you. Once the 14 day quarantine is replaced with something more reasonable we will be booking for what will most likely be a once-in-a-lifetime deal.

  17. Hmm? Only will entice me if 1)no mandatory quarantine of ANY length, 2)no masks in public outdoor setting, 3)no arrests of visitors for freely moving about the islands, and 4)Hawaii recalls its lame governor and replaces it with a sane governor who will not shut down the state for HALF A YEAR while the good citizens of Hawaii suffer…all for 96 Covid “related” deaths (as of 9/11/20_…and Hawaii needs to upgrade their inefficient medical infrastructure to handle health needs, which is a pipe-dream in a state devastated by lack of income and/or tax revenue..for honest heavily-researched FACTS read Alex Berenson’s (famous NYT reporter) book “Unreported Truths about COVID-19 and Lockdowns” Part 2: Update and Examination of Lockdowns as a Strategy….on Amazon who was literally forced by public demand to put this back for sale after they censored it initially

  18. I just checked SWA SJC-LIH-SJC depart SJC March 30 return SJC April 13. Very, very expensive, much more than Alaska Air. I’ll check later this year. Maybe around November?
    Eddie

  19. $99.00 each waxy would definitely peak our interest in returning to Hawaii if we were sure that we wouldwouldn’t Have to undergo a quarantine.

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