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. jody (16 hours 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 (10 hours 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.


  2. Jaden (2 days 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 day ago)

      Hi Jaden,

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


  3. Mary (2 days 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 day 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.


  4. David Smith (5 days 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.

  5. Traveling to Hawaii may 13-20 (5 days 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 (5 days 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 (5 days ago)

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


  6. Glenn (5 days 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 (5 days ago)

      Hi Glenn,

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


  7. David Smith (5 days ago)

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

  8. Nick (6 days ago)

    We will be flying from Indianapolis July 18-26.


    • Beat of Hawaii (6 days ago)

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

  9. Nick (6 days 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 (6 days 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.