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2019 Predictions | When Will Southwest Hawaii Flights Start, Pricing & More!

Exciting times. As 2018 draws to a rapid conclusion, it’s time to review 2019 predictions.

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297 thoughts on “2019 Predictions | When Will Southwest Hawaii Flights Start, Pricing & More!”

  1. Hello,
    I am flying to Maui out of Sacramento from Thursday, 11/15-11/22(thanksgiving) Right now flights are $526 round trip on Hawaiian airlines. Do you think I should wait or book now? Do you predict any sales? Thank you.

    1. Hi Brittany.

      Hard to predict for your dates and route. Gut says you can wait with a target in the $400’s. But only if you’re the adventuresome type.

      Aloha.

  2. Hi,I am looking to travel to Honolulu from LAX May 17 – 23rd of this year for 3 people. I see the airline prices are roughly $573.00 – 626.00. I saw a price drop on Jan 3rd. For 447$ & didn’t realize it was a 1 day sale until the next day when I went to buy. Do you predict anymore drops like that in the next 2 months for May travel dates?

  3. Hello! I have wanted to visit Hawaii for years and look forward to your emails in hopes that one day I can go there! 🙂 I have heard that flights are going down in price, so I am hoping to plan a wonderful trip for my family of five(my kids are 20, 18, and 16) as soon as school gets out in May. I would like to go from MCO, Florida to OGG for about a week-leaving FL on May 25, for approximately a week, then off to Honolulu, Oahu on June 4th and leave for home on June 11th. I am not very experienced with booking flights. My dates don’t have to be exact, but close. I don’t know how to get the best prices/deals. Do you recommend using a travel agent or is it better to find deals online with different airlines? I am also trying to understand the best time to buy tickets. This is a new adventure for us, so I’d love for some advice/tips. Thank you so much!

    1. Hi Kimberly.

      If you aren’t comfortable with doing the planning and buying online yourself, then yes, a travel agent, well qualified and with lots of Hawaii experience, might be very useful. You should budget about $750 per person for airfare, plus inter-island flight. Right now your dates are priced higher, but that should come down over next month or two.

      Hope that helps.

      Aloha.

  4. Hello,

    Planning a trip with several adults and children traveling to Oahu May29-June 5th. Tickets now are roughly $775-$825. Is it better to purchase tickets now, or wait and see if prices will drop?

    Thank you.

    1. Hi Delia.

      You didn’t indicate where you are traveling from but based it looks like Tucson. If you’re actually flying from Phoenix, then there’s a very good chance of lower prices for May to early June. Tucson less likely. But your return date is a Saturday and that probably won’t see good pricing no matter what. So consider changing to mid-week if possible.

      Aloha.

      1. I apologize, yes we will be traveling from Phoenix to Honolulu airport. Traveling dates Tuesday may 29th returning Tuesday June 5th. Will hold out for cheaper tickets, thank you!

  5. Aloha!

    My family and I are planning a trip to Kauai the end of March to the beginning of April. We’re flying from Los Angeles. Do you think the price will drop from $730/per person?

    Thanks in advance for your advice!
    Marissa

    1. Hi Marissa.

      Sometimes with spring break the price does ease up in the weeks just ahead. It’s hard to predict. It could also be unavailable.

      As of today there are $533 nonstops on Delta for your time frame. Xlnt price.

      Aloha.

  6. Great blog post, thank you!

    I’m so excited to take the kids to Hawaii for their, and my, first visit! My boyfriend lived there for a few years, so he’s thrilled to show it to us.

    We’re going to be flying from Boston sometime in early April, we’re open as to dates, as we’re taking the kids out of school for it. Any suggestions? Everything I’m seeing right now is over $700 pp – is that what I should expect, or do you think there are fare drops coming?

    Thank you in advance!

    1. Hi Jenn.

      The best we usually see is in low $700’s and that’s the case for quick connection time flights in April. Not sure it will improve as there is nothing we are anticipating.

      Aloha.

  7. Planning a family trip for 2018 7 adults 3 kids, looking at late June through july, Aug, or Nov Thanksgiving week : LAX to Kona what is best month for flight prices and when should we start looking given the southwest entry?

    Thanks
    Steven

    1. Hi Steven.

      You are looking at two of the most expensive possible times to visit (if it is late June, early July or Thanksgiving). Probably equally so. Not sure Southwest will be here in time for summer, but perhaps fall. We’ll know more about that soon. Mid-August will have good prices on your route if you wait. So, if that time frame works for you, and you’re a betting person, try holding off. Otherwise, you’ll have to pay up.

  8. My husband and I are planning a trip to Hawaii for the last two weeks in October 2018. Our trip will be open jaw: going from ORD-HNL non-stop first class on United (the only non-stop from ORD), one week on Oahu, then inter-island from Oahu to Maui, one week on Maui, then OGG-PHX or another west coast city for one overnight before flying to MKE. We would like to fly first class for the non-stop and the flights home. I have been monitoring prices but I have no idea what a good price would be. How far in advance should we purchase these flights as well as the inter-island flight and at what price?

  9. Hello love your blog and advice! I’m scheduled to fly to lax on July 7 2018 and not worried about getting to Hawaii from here that seems easy! Coming back to east coast looks challenging on July 19th. I have a lot of delta points which woukd help on 2 tickets. Do you thibk delta is the way to go to Pittsburgh and if so woukd you spring for first class? Talks of the different planes confuse me. Woukd you recommend first class and is 850 one way reasonable? Many thanks! Melissa

    1. Hi Melissa.

      Thanks! $850 in first class is reasonable for summer. You can look at a site like seatguru.com and see seating on various flight options. Probably we’d pick the 767 via MSP or ATL from HNL for wide-body and better first class.

      Aloha.

  10. We are looking at going to the Big Island and Kauai from the Bay Area/Sacramento in late July-flights are now $758 roundtrip including the interisland flight-do you think it will get cheaper or should we book now?

    1. Hi Ryan.

      Since 2018 will be anything but normal in Hawaii travel, yes it might go lower. Suggest waiting if you have flexibility. Also, can’t say when it might change, but chances are good you’ll thank us. 🙂

      Aloha.

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