The Cheapest Time to Fly to Hawaii 2014

The Cheapest Time to Fly to Hawaii 2014

When is the best time to travel using cheap Hawaii deals, airfare in particular, and when should you book? The number one question we’re asked is “when is the cheapest time to fly to Hawaii.” Here’s our 2014 update.

Overall, Hawaii deals will be best for travel from mid-August through early December.

When to Travel

  • August 18, 2014 through November 14, 2014 and to a lesser degree the first two weeks of December 2014 are the best dates for a reasonably priced Hawaii vacation this year.
  • These are the most economical times to visit Hawaii in terms of all costs, including airfare, accommodations and activities. As a bonus, you’ll also find the very best Hawaii weather of the year.
  • Lastly, there’s nothing like the feeling of having Hawaii all to yourself, and again this is the time of year to best achieve that experience. Spontaneity in all things Hawaii is possible in the fall. A fall Hawaii vacation gets our unequivocal thumbs up.

When to buy

This largely depends on your flexibility and how determined you are to take a Hawaii vacation. Sometimes the deal that is available now is the best option even if it isn’t the rock bottom price, rather than one that may or may not materialize later.

Hawaii deals for fall travel may begin to appear starting in summer, any time from June through September. That timing depends solely on whether airlines need help from lower airfares to fill their seats. If they believe they do need help, expect deals sooner. If demand is adequate, however, fall sales may not appear until September or even later.

We have our fishing net out to catch Hawaii deals for you and will reel them in and be the first to let you know when they appear.

What to pay

We expect to see round trip fall Hawaii airfares from many west coast departure cities to most of our island destinations priced from $450 to $600 including all taxes and fees. Midwest and east coast cities will usually run about $250 to $300 higher. It is sad to note these low season fares are up significantly compared to prior years.

Some cities have increased competition. Travelers using these gateways can expect to benefit most in terms of best pricing and greater availability. Those are San Jose, Oakland, Seattle, Bellingham, and San Diego.

Vip Alerts


  1. Lisa (14 hours ago)

    I am planning a wedding in Kona for the week of June 27 – July 5 and have been watching the flghts daily and there hasnt been any change in the past several months. We can fly out from PDX or SEA. Should I just bite the bullet and buy the tickets now? They have been hovering around the $900+ range and the seats are filling up. I have the $99 companion fare with Alaska and was going to use that so that would bring it down to about $500-$600 per ticket.

    • Beat of Hawaii (10 hours ago)

      Hi Lisa,

      Suggest buying now as those are the peak dates of summer and could even sell out.


  2. Joe (3 days ago)

    Hi, I am planning a trip from Boston or New York to Maui and Oahu at the week between Dec 23rd to Dec 30th. Now I can find Alaska Airline offer $1200 (BOS to OGG and HNL to BOS) with 1 stop each way. From some forums, people previously got good deals on early fall for the airfare during Christmas week (~$800 to $1000, depart from East coast). Is it too early now to book a flight on Christmas? What will be the good time and good price to book a Christmas trip based on your expectation? Thank you very much.

    • Beat of Hawaii (3 days ago)

      Hi Joe,

      You can’t really draw conclusions from what happened before. We are in an entirely new situation in Hawaii travel. Having said that, $1,200 is probably fair for your dates. If you wait you may see lower airfares on the actual holiday days and the eves (12/24 and 12/25) for example. And there could even be somewhat lower prices for the holidays, although probably not lower by much if at all and no one knows when that could occur. None of it is guaranteed and if you are determined to visit, you may need to just pay the price.


  3. Helen (5 days ago)

    Good Morning,
    I live on the eastcoast (phl) looking for a flight to maui for 11/1-11/8/2014. When should i purchase airfare? Would it be better to flight to the west coast to connect to maui? Thanks for any help you can provide.

    • Beat of Hawaii (3 days ago)

      Hi Helen,

      If you travel on 11/2 instead of on 11/1 the fare is $857 instead of $961. You could wait for the potential of fall airfare sales (which could happen from June on) from either New York or a west coast city like Oakland. But traveling with another city brings in the possibility of missed connections that even travel insurance does not cover. And PHL doesn’t see many Hawaii deals as you probably know.


  4. Bianca (6 days ago)

    I’m planning on taking my husband to Honolulu Hawaii for his birthday in August. We would like to leave Friday 8/22- Sunday 8/24 round trip, when would be the time to buy and what would the cost look like?

    • Beat of Hawaii (6 days ago)

      Hi Bianca,

      Are you traveling from Los Angeles? If so you might want to try checking Allegiant as they have fares around your dates for about $400 round trip. Otherwise it will be around $600 round trip on other airlines. It isn’t clear that there will be any sales before then.


  5. Del (6 days ago)

    Is it too soon to purchase tickets to Kauai from Los Angeles for September? I’m seeing the lowest fare at about $640 round trip, flying Sunday to Sunday. (Condo is already locked in for those dates.) Is that a good price, or should I wait for them to drop?

    • Beat of Hawaii (6 days ago)

      Hi Del,

      It is a “fair” price. So with condo dates locked it, it might be better to buy than to wait.

      This is an odd year in terms of the airlines’ pricing of Hawaii. Until something changes, we are going to continue to see fewer deals than is normal.


  6. jody (1 week ago)

    I am looking to fly to hawaii, either kona or hilo in august around the 20th to september 2 or so. When should I start looking? I would be flying out of the east coast, newark. What are the best times to book the flight and do the prices go down on Tuesday nights as they say? or are should i call the airlines?
    I was sad that I did not have the money 2 months ago as the airfare was 650 dollars round trip.
    If we wait will we get cheaper prices?

    • Beat of Hawaii (1 week ago)

      Hi Jody,

      Right now fares are running quite high. I see a $734 round trip to Honolulu on the UAL nonstop if you can leave on the 19th. Then you’ll need to buy inter island flights. Fares might come down, but this is an unusual year in Hawaii travel, so it is difficult to predict.

      Calling the airlines never works.


  7. Jaden (1 week ago)

    I’m wanting to go to Hawaii August 11-18. When would you say is the best time to book them?

    • Beat of Hawaii (1 week ago)

      Hi Jaden,

      Start looking now. We might see late summer Hawaii deals but that definitely isn’t a sure thing.


  8. Mary (1 week ago)

    I am planning a trip to Kauai, leaving between Christmas 2014 and New Years. I’m wondering if I should purchase flight tickets now or wait for possible lower fares.

    • Beat of Hawaii (1 week ago)

      Hi Mary,

      Suggest purchasing as soon as possible as that is the time of highest annual demand. If you are able to fly on the holidays or their eves, the prices can sometimes be better.


  9. David Smith (1 week ago)

    I have to make a correction. This morning (4/10), I stated that flights on Hawaiian Air were running $198. They were actually $178 from Oakland to Maui on 7/10, and $228 from Maui to Oakland on 7/27. When I returned to the website 1/2 hour later, they were asking $850 RT. I just happened to hit at the right moment, and my tickets we’re $446RT. My advice is to keep checking as many times as you can during the day. We were actually going to cancel the Maui trip this year, and go elsewhere because the fares were so high.

  10. Traveling to Hawaii may 13-20 (1 week ago)

    Hey Im currently looking into purchasing the tickets for two people but the price increased $71 since this past Tuesday…Im wondering if I should cut my loses and purchase them now or will they be cheaper come next week tuesday-ish?

    • Traveling to Hawaii may 13-20 (1 week ago)

      Im flying from Chicago to Honolulu….So I take it prices will continue to increase now? and this past Tuesday was the cheapest at $800?

    • Beat of Hawaii (1 week ago)

      The rate today is $818 on UAL with one stop and $1,090 nonstop. That may or may not improve.


  11. Glenn (1 week ago)

    I’m sorry, I don’t see any of these fares from OAK to OGG, either on HAL’s website or KAYAK

    Just noticed this morning (4/10/14) that Hawaiian Airlines has seats as low as $198 RT from Oakland to Maui in July.

    Beat of Hawaii (10 hours ago)

    Aloha David.

    Yes, and event better to Honolulu.

    • Beat of Hawaii (1 week ago)

      Hi Glenn,

      We have revised this to reflect that Hawaiian raised the prices within 30 minutes of our publishing them.


  12. David Smith (1 week ago)

    Just noticed this morning (4/10/14) that Hawaiian Airlines has seats as low as $198 RT from Oakland to Maui in July.

  13. Nick (2 weeks ago)

    We will be flying from Indianapolis July 18-26.


    • Beat of Hawaii (2 weeks ago)

      July 17 to 27 would reduce the cost by $200 if that helps Nick. On US Airways/American.

  14. Nick (2 weeks ago)

    My family and I are planning a trip to Honolulu for July 18-26 of this year (2014). We’ve been doing research and looking for airline deals for several months now and most places say book 3-4 months in advance. We are in that time frame now and prices have been holding steady at around $1200 per ticket. Do you know if these prices will drop in the coming weeks or do you have any other tips for us to find a cheaper price?


    • Beat of Hawaii (2 weeks ago)

      Hi Nick.

      You didn’t say where you are flying from, but this should cover it. July is a very expensive time to visit Hawaii and that is true every year. You can try varying your dates by a day or two if you have the flexibility as some days of the week may be higher or lower.