53 thoughts on “NEW Southwest Airlines Hawaii | Is This a Winning Strategy?”

  1. We are flying to Maui 3-31-18 for one week (Easter week). Any chance Southwest will be flying to Hawaii by then? Also, should we hold off booking our flight even if Southwest will not be flying to Hawaii by then? Right now, with Easter week, the flights are very expensive.

    1. Hi Bill.

      No Southwest will not be flying. Also spring break is always expensive and next year won’t be different. You can wait until last minute if you’re okay with not going or paying more if it doesn’t work out. Otherwise for that high season, best to book now.

      Aloha.

  2. We have a condo booked in Maui in late April 2018 but have been holding off on booking the flights (non-stop preferred from San Diego) in hopes that Southwest will be servicing Hawaii by then or that the anticipation will result in lower fares, but so far we havne’t seen this occur. As far as I’ve seen, there hasn’t been an announcement of the beginning of service yet, am I correct?

    1. Hi Dean.

      Not expecting that to happen. There could be new flights from HA from San Diego but not positive on that either. About $450 now but hang out a bit and should improve somehow. We’re thinking price target of about $100 less.

      Aloha.

  3. I would love to see more (re: any) affordable options out of the Midwest. Cheap from the West coast, yes, but to get to CA or WA from the Heartland is really pricey.

  4. Aloha, we have a Hotel reservation and return ticket it for Maui dec 17,2017
    As well as a return flight and I have been watching prices to get there
    But it doesn’t seem be dropping yet. I have an app called hopper that predicts pricing dropping below 300 and I have reas here to watch for last minute deals… so my question is how last minute should I wait?
    And do you know anything about how hopper makes their predictions? Let me know, Mahalo

    1. Hi Joseph.

      Wouldn’t think Hopper knows much frankly. Not sure what you’re asking about. You didn’t list cities and dates in any way we could understanding. We need something like I’m looking to fly between X and Y oin this specific date range and what can be expect price to be. Sorry to not be able to help.

      Aloha.

  5. Looking for nonstop or one stop flights on Southwest from Boston or Manchester, NH, to Maui in late Feb. Any chance this is going to hhappen by then or any time soon after?

  6. I live in Sacramento, CA and have family living in Kona on The Big island of Hawaii. I have not found any direct flights from Sacramento to Kona. When flying Hawaiian, we fly to Honolulu then have to island hop to Kona for an additional charge or United flys to Los Angeles then to Kona but we have to pay for the additional stop. I’ve seen larger Alaskan Airline airplanes land there so I don’t understand why there is no direct from Sacramento. Although with Sacramento being one of Southwests main hubs, we’re crossing our fingers they will offer direct to Kona. What do you think?

  7. I am loving all the intel. Thanks so much for keeping us all in the loop.
    My question is about purchasing flights for March 2018. We have rigid plans to fly on March 24, so I missed the opportunity for the crazy cheap flights from the west coast because those dates ended on March 22. Any thoughts on lower fares for the last week of March out of California? We’re in LA, but could also fly out of San Francisco.

    1. Hi Rebecca.

      That’s the peak of spring break so really don’t expect to see any improvement. There is a remote possibility of new flights coming by then but you’d have to be willing to take a chance that it won’t work out. Right after that next spring things should get better with the new planes coming to HA.

      Aloha.

  8. Aloha we are flying to Kauai in June 2018 and have not purchased our air flight yet. Can we expect to see a drop in flights to Kauai in June? Should we wait to book?
    Mahola

    1. Hi Donna.

      For next year it might work to gamble and not purchase tickets in advance. That is in case you are the adventuresome type. We don’t know for sure, but it is looking good for unusual discounting next summer based on everything we know and have been sharing. If not, then buy now but don’t look back.

      Aloha.

  9. Thank you for all the intel and insight on SWA to Hawaii. Exciting times for sure. I read with envy all the great airfare deals to Hawaii from the West Coast the East Coast and a sprinkling of other areas. We are not so lucky out of IAH here in Houston. United owns the non-stop market and prices their coach fares that way. It is absolutely ridiculous and if I want to use miles…wow…

    We’re really hoping SWA will affect United’s choke-hold on Houston.

    1. Hi Keith.

      We’re hoping for the same thing. SWA will certainly be bringing people from across the US to Hawaii and that has to be part of the planning.

      Aloha.

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