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.

      Aloha.

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

  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.

      Aloha.

  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.

      Aloha.

  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.

      Aloha.

  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.

      Aloha.

      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.

      Aloha.

  9. Love subscribing to the email for alerts. Thank you. Planning on a May 2018 trip to multiple islands from Las Vegas. Can I plan on a Las Vegas sale coming up?

    1. Hi Tammy.

      Gut answer is yes you can. Don’t know for sure what’s going to be happening in terms of LV routes, but we’re hopeful to see new flights.

      Aloha.

  10. Hi,

    We are planning a trip to Honolulu from the Bay area from November 17 to November 23, 2017. Any suggestions for best pricing? We have been tracking fares on various airlines since last week. Return fares now are just shy of $800 per person vs last week when we saw $657 on United. Any ideas? Thanks in advance.

  11. Oahu, First week in April, when should I buy and what is a “good” deal for that time of year?

    1. Hi Kathleen.

      From mid-$400’s to $600 depending on day of the week. That is spring break so prices are very fair. Not sure if they will improve. Could closer to travel dates, but not certain.

      Aloha.

  12. Hi, traveling from Ft. Lauderdale to Kona, sometime in the month of October. Should we buy flights now or wait?
    Thanks!
    Julie

    1. Hi Julie.

      There are some $700 fares with good connection on Delta. Do a flexible date search to find. That’s a good price to buy now and not likely to improve. Otherwise fares are running up to about $900 or more.

      Aloha.

  13. Heading to HNL from BWI (Baltimore) Fri April 13 2018 returning Tues April 24.
    Found RT on Alaskan Airline for $794.
    American Airline $888.

    The Alaskan site shows Alaskan flight for the whole trip; no other Airline. I’m Hearing Alaskan buys seats on other airlines so you may not actually be flying Alaskan. Of course with Airline (plane) change you would/ could entail additional check bag fees.

    If Alaskan does buy other airline seats would it not show on the site so you would know what you’re purchasing / what Airline you’re going to be on?

    Also with the above pricing for Alaskan and for American and not traveling till April 2018 do you think it would be better to wait to purchase tickets through either Airline??

    Sometimes less expensive is not always the better deal. 🙂

    Thank you very much for your response and bearing with me on my long-winded message.

    1. Hi Linda.

      If buying on the Alaska Airlines site it will be clear if it is their flight or some other airline’s. There should be no confusion. You can always call them to clarify.

      There is no rush to buy for those off-season dates. If you wait, price target is sub $600. Could happen from fall to winter.

      Aloha.

      1. Thank you for your response to my questions. I feel much better and will call the airline for clarification if a doubt remains when booking the flight. Thanks again. Looking forward to this trip!
        Aloha.

  14. I’m looking at a family trip to Kauai in early April from Salt Lake City. Should I book a package deal now or just housing and wait to see if airline prices drop.

    Thank you for the helpful info in your emails.

    Thanks

    1. Hi Howard.

      Early April is going to be spring break, so probably no reduction coming for that. Starting 2nd week in April that is definitely possible and thus suggest waiting with price target of just under $500.

      Aloha.

  15. What are the chances that fares from San Francisco to Kauai will go down by the end of the month? Our RT is Sat Sep 30 to Sat Oct 7. Thank you!

    1. Hi Sandra.

      Flying on those Saturdays looks like it will stay expensive. Mid-week saves a bundle if you can swing it.

      Aloha.

  16. Hello,

    I love your website and valuable info! My family and I are planning a trip in late Feb from the Bay Area. Current sale price is $198 each way. Is it likely that prices will continue to drop, or should I buy tonight?

    Mahalo!
    Allen

  17. It looks like most deals are from the west coast. Can we expect any deals from Denver for January 2018?

    Love this site!

    Thank you.

    1. Hi Ron.

      Watch for fares in low to mid-$500’s. Not available yet but should be by fall.

      Aloha.

  18. Hello,

    I’ve been waiting for price drop from LIH to PDX. Leaving as soon as possible. Looks like United or Hawaiian but everytime I try to get the special price drops like this one…they don’t reflect n the carriers site? Is there a promo code I’m missing?

    Thanks so much for all you do, always go to Beat of Hawaii when traveling!

    Zoe

    1. Hi Zoe.

      That fare between LIH and PDX is still widely available through early December except Thanksgiving. There is no promo code and you’ll find it directly on the Hawaiian Airlines website. Use monthly date search to help find available dates. Some weekends but mostly mid-week.

      Aloha.

  19. Aloha,

    I have been keeping up on updates since I discovered you guys! What a great, helpful site you’ve made. =) I love it! I know prices were down early this month, but the flights I’m looking at have gone up $35.00, it’s not bad for one person, but adds up for my whole family.. We are planning on Oct 25-Nov 5. Do you think prices will drop again around Labor Day? Or should I just bite the bullet and purchase at this price. (SJC-HNL was $189 on 8/2, today $219, and OGG-SJC was $219 on 8/2, today is $224) Many Thanks for your time & input!

    1. Hi Mimi.

      For your dates we’d suggest waiting. In the next week or two there will undoubtedly be another round of fall sales and your routes and dates should work into those.

      Aloha.

      1. Aloha,

        I just saw the news in price drops! The flight home on a Sunday from OGG did go back to $219 (11/5/17), but going to HNL on a Wednesday is still at $219.00 (10/25/17). I know you mentioned to sit tight for the next couple of weeks, just checking if you still think that.. Thanks! =)

        Mahalo, Mimi

  20. Hi! Just curious if you think there is any rhyme or reason to me booking a trip to the Big Island at the same time as I did last year? After watching airfare prices up until early Oct of 2016, I purchased airfare for $397 RT for Mid Dec of 2016 out of San Diego. I’m thinking of going the same time this year (maybe more early Dec this time). Do you feel there is any safety to waiting until the same time this year? If it hits that price point between now and then, I’ll buy immediately but if it doesn’t, what are your thoughts?

  21. Hi. I’m thinking of going to Hawaii from Jan 12 – Jan 16. Fly from San Diego to HNL. Right now the fare is $560 on HA. Is it a good deal?

    Thank you.

    1. Hi Annie.

      Could come down if you wait and we suggest doing so. Target price is about $475.

      Aloha.

    2. My husband and I are looking to travel round trip from DFW to Kauai for one week and then to Maui for one week. October-November time frame. I have only seen that AA that offers non stop flights in first class. We are flexible on dates and would look at flights with one stop if the layovers were not terribly long and hopefully have premium seating. I truly appreciate any advice you all have for us.

      1. Hi Mary.

        The Kauai nonstop doesn’t start until December. Best connections seem to be on American and the price is about $2000+.

        Aloha.

  22. Aloha, I’m looking for a flight to HNL from PDX on 4/18/18 – 4/21/18, but i couldn’t the $218 as advertised, I’m being qouted $556.

    I think I’ll have to wait and see if I can get better deals by Decemberish…

    Thank you,
    Romeo

    1. Hi Romeo.

      “Travel from the mainland or Hawaii largely between mid August and mid-November….” That was never available for your dates. Could come down depending on when new routes between Phoenix and Hawaii are announced.

      Aloha.

  23. Hello – I’m interested in planning a family trip to HI for my husband’s 40th birthday on September 18th. How is the weather during this time and are there any special events happening? We’ll be travelling with our children, ages 6 and 8. Thanks in advance for your recommendations.

    1. Hi Natalie.

      Great time of year to visit – perhaps even the best time for weather, less crowding and better value. You’ll need to Google for events, depending on which island you’ll be visiting.

      Aloha.

  24. Hi, where can I find the deal from San Diego to Oahu for 220.00? Planning on traveling end of October through 1st week in November. Thank you

    1. Hi JoAnn.

      It is available during that time frame. Click the link that goes to Hawaiian Airlines then put in your cities and view monthly calendar of fares or check day by day.

      Aloha.

  25. We are flying to Maui from Portland, Oregon, on December 4th with our return trip to Portland on December 14th. Any thoughts on how long we should wait to purchase our tickets in hopes of the best price available? Please and thank you, Julie

    1. Hi Julie.

      There is $366 round trip available per today’s post – and for your specific dates. Good connection – 1 stop. Nonstop is nearly $300 higher and best hope for that is probably low $500’s which might occur any time between now and then.

      Aloha.

  26. Aloha!

    My family of four plus infant plan to fly back and forth midweek to Oahu – SF Bay Area for the Lantern Festival. Should we purchase now? If not now, when do you recommend we purchase?

    Mahalo!

    1. Hi Michelle.

      That takes place in May. Watch with us for post spring break deals late this year to early next year.

      Aloha.

  27. Hi! I am wanting to take my family on a Hawaiian vacation. I heard February is a good month to go. There will be 9 adults 3 children under the age of 7 and 2 babies under the age of 2. We would be traveling from Ord, and would really like to see Pearl Harbor area for 7 days. What I am finding is too much money. Any ideas?? Thank you in advance! TONI

    1. Hi Toni.

      Check with multiple carriers’ group travel desks. That applies when you have 10 traveling together. Hope that helps.

      Aloha.

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