Don't Make These 11 Hawaii Travel Planning Mistakes

Updated Hawaii Vacation Deals $356+ RT | Today Only

Fares changed again this morning on flights to Maui, Kauai, Big Island and Oahu. See Beat of Hawaii for details.

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135 thoughts on “Updated Hawaii Vacation Deals $356+ RT | Today Only”

  1. We are flying into Maui on March 7 using my American miles but do not have a returning flight yet. We want to fly back to Denver on March 17 : 4 adults, 2 children, and a lap baby. One way flights seem pricey right now from Maui to Denver and we are trying to get a flight with a short connection because of the kids. I check American airlines daily but flights using a reasonable amount of miles have not been available. When should I buy? Any help and suggestions would be greatly appreciated.

    1. Hi Judy.

      From $430 one way on your date which is suffering from it being spring break. Mid-week a week earlier and the cost is much less. Also varies by connections and duration. Doubtful your date will improve much if at all for those reasons and not sure what else we can suggest.


  2. We live in Boston and go to Hawaii every December 21st to January 3th but never see a deal from any airlines

  3. Hi. We have a family of 6 (4 adults, a future 5 year old and a 15 month old flying March 10 returning March 24 to Lihue. We would like seats together. With new airlines going there the end of December and early January, should we wait to schedule? I am not sure if this is during peak spring break or not. Any advice would be appreciated. Thanks! Pam

    1. Hi Pam.

      A little too early for the great deals we’re anticipating and yes, you’re flying in spring break. You didn’t say where you are flying from. But generally speaking, if you’re set on those dates, it might be best to book sooner than later.


  4. I’m so thrilled with your website, I have shared it with lots of folks! We returned from a family trip to Maui via Portland, Oregon. Thank you so much for all the travel tips you provide on your website. I am becoming quickly addicted to Hawaii travel! I’ve only made it to two islands thus far… I look forward to visiting Kauai and Kona in the future! I’ll definitely be using this website to help plan!!

    1. Hi GL.

      Thank you. Glad you’re enjoying your Hawaii travels and Kauai and the Big Island both have so much to offer, and are so different compared with Oahu and Maui.


  5. Last year we got flights from ORD to OGG for about $1100 to $1200 from Dec 27-Jan 12 in August. This year rates are $1370. Are rates going to go down soon? We only like to do non-stops but we’re hoping the rates drop soon.

    Love all the updates on fares and wish you would report more often from Chicago or other midwestern cities too. Seems like the West Coast gets all the attention.

    1. Hi Julie.

      If there was anything more to report from eastern cities, we’d be all over it. It seems like more flights from further east will happen in the not too distant future.

      We are seeing $1015 RT on your specific dates, nonstop on United. One-stop starting at under $800.


  6. Hello, we are looking to travel to Kona or Kauai from Washington state (PSC, GEG, SEA, or PDX). The dates are November 3rd – 11th. When do you think the best time to buy is? This is for a family of 4.

    Mahalo, Pete

    1. Hi Pete.

      Watch for another sale within the next week or so that will included SEA and PDX for your dates.


      1. Did I miss the sale? It’s 9/11 and PDX to KOA is $667 on Alaska. I’d like to fly non-stop as I will be with my elderly parents.

  7. Aloha, I need to buy a ticket from Bay area (preferably San Jose) to Hilo or Kona during prime Christmas dates. Ideally Dec 23- Jan 2. Right now tickets are over $1300

    Should I keep waiting for better deal or just grab it before it goes up ?
    Thanks do much!

  8. I’m planning 2 trips to the Big Island. Nov. 15-19 and Dec.11-18. I’ve been watching prices. Best price was in July San Jose to Hilo $475. Wasn’t ready to purchase several tickets then, so I lost out. Will it drop to that price again? Or when is a good time to buy? Thanks for this site!

    1. Hi Lydia.

      It looks like you’re interested in flying SJC-ITO only, so we’ll base our comments on that routing. $647 for your first dates which are touching Thanksgiving break. $527 for your second trip. Not too likely this will go down so suggest buying now. These are on Hawaiian.


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