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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. We are looking to book from Midwest to Kauai in October. Prices are currently 800-900. Trying to decide if we should wait to book in hopes for lowering prices…I know no one really knows, but any expert advice?

    1. Hi Sarah.

      Without a specific city it is hard to give more details. Overall, fall fares aren’t optimal yet and should improve over the next couple of months.

      Aloha.

  2. My husband and I will fly First Class one way from Maui to Phoenix but refuse to take the American Airlines all night flight on an outdated 757. American adds a “seasonal” flight OGG – PHX in December but not before we depart 12/8. Looks like Hawaiian has the newest equipment but would not earn AAdvantage miles on flights from HI to the mainland. Thanks for any suggestions.

    1. Hi Laurel.

      Not sure what else we can suggest. You could look at transiting Honolulu for more options, but that’s a bummer too since it wastes so much time. Hawaiian lie flat will beat old 757 first, but as you said, no miles.

      Aloha.

  3. Hi can you tell me which islands southwest will be flying in to? Departure would be SJC

    Please and thank you ☺️

    1. Hi Marta.

      Flights will be to Maui and Honolulu at the beginning. Other flights, including Big Island and Kauai, plus inter-island will follow.

      Aloha.

  4. I have been saving for 8 years to take my grandkids in Feb. do you think I gave a chance to get flights then? That lie so late? Please help!

  5. Yikes! Do we keep holding out for SW to start flying? Our dates are Feb2 – March 3. My husband is getting nervous and doesn’t want to wait any longer. We fly out of Spokane to either Honolulu or Maui. We have an Alaska companion fare card but return flights aren’t so great. I just know once I book, SW will start flying!

  6. Aloha,
    Just wanted to say that you folks do a great job here on this site. You have the most information anywhere with updates on Southwest starting service to Hawaii. Keep up the good work. I check here every day for our planned trip at the very end of February to Maui.
    Thank you!!!

  7. How do you see all the new routes, increased routes and lower airfares will affect the islands? Of course tourism brings in money but what about environmental impact on beaches, oceans, coral reefs, hiking trails, traffic etc.? Do you foresee the costs of hotels, car rentals and restaurant costs to increase?

  8. Id say that a better sign that the airline is coming soon to Hawaii is when there is an employment call for anyone to apply for jobs at the airport for Southwest and the arrival of their ETOPS test flight to Honolulu. You also have to factor in the completion of the new terminal that Southwest is intending on using, along with the arrival of company material – boarding gates, carts, tugs, etc. – Have any of that stuff been seen on ground in Honolulu yet?

  9. Traveling to Honolulu, Hawaii mid April, 2019 from Philadelphia and returning on the 27th.
    Can you please advise when is best to book airline tickets.
    Thanks so much.
    Karen

    1. Hi Karen.

      Probably best about 3 or 4 months in advance. Best hope for price is low $500’s, but anything from there up $100 or so would be great, with a good connection. Should work out.

      Aloha.

  10. I’m traveling with my family in Mid June 2019 to the big Island for a week (Wednesday to Wednesday), when should I book our fair?

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