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. Wow, your email came to me at 4:24 p.m. I looked at rates between 10/11 and 10/17 (mid week flight should be in that bargain bin) at 4:31 p.m. between both PDX and SEA to HON and both were both at double or triple the price. Comments?

  2. Hi,
    I am looking for flights from San Francisco to Honolulu march 23rd-April 1st. I know it’s peak season since it’s spring break. Should I buy now or hold off a little while. Cheapest now is around 760.00 round trip.

    Thank you
    Ardith

    1. Hi Ardith.

      Your dates sit right in the middle of spring break. Therefore gut says you’ll do better to buy now. Price if fair for those dates.

      Aloha.

  3. There’s rarely any love for Chicago. It’s usually the West Coast or NYC with the AA/ UA hub of ORD being an after thought.

    1. I hear ya..I live in Northern Michigan so not only is Detroit a good 4 1/2 hour drive-tickets are easily high $800s if not into $1000 pp
      I would drive to Chicago for a $400 flight no problem!

  4. I clicked on the San Diego to Kauai $202 link and it took me to HA site that didnt mention that fare at all.

  5. Hi, Flying in to HNL for a week then off to KOA for five days and finishing in Maui in 3rd week of April in to May when is the best time for inter island flights. there are four of us/ Thanks your newsletter is great

    Rich from Florida

    1. Hi Rich.

      Fares inter-island don’t vary all that much – sale or not. But there should be some price breaks for that post spring break period. Perhaps 30-60 days in advance.

      Aloha.

      1. Hi there, what is the policy with Hawaiian Airline if I purchase Inter Island flights for late April and early May do they will they refund the difference in price if the fare goes down? When is a good time to purchase for multi ticket and Islands

        Thank you so much for the response and advice. I am looking for when should my sister buy their tickets from Philly to HNL then leaving from OGG in April 21 or 22 and returning May 5th or 6th. Mahalo! for all you help

        1. Hi Rich.

          1. No they will not refund the difference. It won’t be large enough to bother with anyway.
          2. Start checking fall of this year and plan to purchase by January.

          Let us know how it goes.

          Aloha.

  6. Hello again! What I was attempting to ask in my last question was: if I have to buy last minute one way tickets from Hilo to Sacramento, in September will it be very costly?
    Or will the prices continue to drop? Likely?
    We have one way tickets now, and hoping to stay like ne’er but if I cannot do that, will it be crazy expensive?

  7. Great information. Great site. We will be flying home from OGG-BOS in early May 2018 (On a Saturday). Do you have any idea when the best time to purchase flights would be? They are currently running at about $380? Should we wait? Thanks, Dave

    1. Hi Dave.

      Thank you. Next year is a bit up in the air (decidedly more so than usual) because of new fleets and potential new carriers in our market. Putting all that aside, that’s a fair price for buying now. We have a bird in hand vs. the bush situation.

      Aloha.

  8. Hi there,

    Love your site! We are looking to travel to either Maui, Kauai, or Oahu the week of January 20-27, 2018, flying from Los Angeles. We are also Southwest Rewards members. Do you have thoughts 1) the best time to buy, and 2) what an anticipated “deal” price might be?

    Thanks so much!

    1. Hi Susan.

      Thank you.

      Probably late fall will be best time, as we’re hoping new routes and more competition might appear by then. If that doesn’t happen, then given you’re flying on Saturdays which are more expensive, you might need to target up to $600.

      Aloha.

  9. Aloha,
    I have been keeping an eye on the flights from the west coast (bay area) to lihue. Do you think flights in early November will be lower than the current $600.00 if I wait until Sept to book? Your best advise good or bad. Mahalo! Karyn

    1. Hi Karyn.

      There are many RT fares of under $500 in November, so you must be talking about Thanksgiving week. In that case, no it is not likely to go down.

      Aloha.

    2. Hi Karyn.

      Midweek fares from SJC are $461 for November. That’s about as good as we expect to see.

      Aloha.

    3. Aloha! I look forward to your email alerts and helpful information. It’s great there’s more competition right now but as I’m looking at flights to Kona from LA for either late August or early September and as far as late September, they still seem a little higher versus last year. Do you think it’s a good time to buy given the sales, or will prices drop even lower? I’m flexible on dates so I’m looking for the best deal. Mahalo.

      1. Hi April.

        There are $488 RT fares on Hawaiian last week of August and in September – nonstop. Good price and highly unlikely it will improve.

        Aloha.

  10. Going to Maui for a wedding Dec 13th – Dec 22nd, flights currently $591 (direct flight out of LAX) Good deal or wait?

    Thank you for your help! 🙂

    1. Hi Stephanie.

      Probably a fair price given the fact that your return is very much high season. Consider buying now.

      Aloha.

  11. Hello, I’m planning a trip to The BIG Island (HNL) with my daughter in June 1st-11th 2018. This will be our first trip to Hawaii. We are flying from Ohio. When is the best time to purchase my tickets? I’m glueless when it comes to the best time to buy. Looking forward to your reply. Thanks

    1. Hi Pete.

      Well departure date is low season and return is high season. Not sure whether you mean Big Island or Honolulu. Also Ohio has different airports. Looking at Cleveland to Honolulu, it’s pricing at about $1,100 RT. It could improve, but since return is high season, not sure. Best suggestion is to wait until spring to book. Probably won’t go higher and could improve.

      Aloha.

      1. Also, you could save yourself a few hundred dollars just by departing/returning a couple weeks earlier if your dates are flexible at all.

  12. Hello! Considering buying one way as we are considering a stay of a couple months or a move….. if it does not look like a good idea we will need return tickets 9/14 or so to Sacramento from Hilo. Should we risk waiting or buy them round trip and add trip insuraance? Please advise.
    Thank you

    1. Hi Stephanie.

      Not entirely clear what you are asking. So generally, one way tickets to Hawaii are sometimes just 1/2 of round trip. But you need to check as it isn’t always true. Flying ITO-SMF on 9/14 approximately, should not be an issue as that is off season and availability will be good.

      Aloha.

    1. Hi Jeanette.

      Good question. They fluctuate, but generally much less so and they are almost never part of a “fare sale.”

      Aloha.

  13. need direct flights from Portland Or. to Big Island Hawaii Too difficult to get there because you have to land else where on the west coast first or land in Honolulu either way it’s a bunch of malarkey Please help Thank You Buckley N

  14. Thanks for keeping me up to speed on Hawaii flights, a follower for many years now. Lax to HNL oct 14-24. Should I buy now? When’s the best time to buy tix for the family?

    1. Thanks Jon.

      Tricky market with new competition coming to the west coast causing more variability than usual in fares. Gut call is to wait with target of $500 or less. Keep a lookout – we will too.

      Aloha.

  15. Hi,
    We a trying to plan a trip from Chicago to Kona or Lihue. We are open to dates, but leaning toward Jan or Feb of 2018. Any tips on finding a lower airfare? The lowest I have found is around $800 RT.
    Thank you,
    Maria

    1. Hi William.

      That departure date could stay expensive. Otherwise, unless you want a 19 hour duration at just under $800, fares are near $1,000 with a 12 hour duration. Optimal is low $800’s with fast connection. Might happen, but can’t say for sure or when. Just keep watching.

      Aloha.

  16. Just an idea. Perhaps start adding fares from Vancouver BC. Sometimes Air Canada and Westjet have seat sales. The prices are always in C$ which when converted back into US$ could represent a major savings for American travelers. The flights are always non-stop so no need to waste time transferring thru LAX or SFO. YVR is 40 minutes from the border at Blaine WA.

  17. Hello,

    A group of 4 of us are looking for fly from New York area to Kona September 25, return October 6th. When is the best time to purchase tickets?

    Thank you!!

  18. We are planning on traveling from Dallas to Kona October 1-13. When is the best time to purchase tickets? Do you think the prices will lower later in the summer? Aloha.

    1. Hi Diana.

      Just keep watching for best rates. Your days of week aren’t optimal for best pricing – midweek is better. Otherwise looks like $800’s on your exact dates, but return a day earlier for example and price drops over $100. Availability shouldn’t be an issue.

      Aloha.

  19. I’d like to see deals from the east coast to Hawaii, I would travel there more if I could get a good fare from Orlando, fl instead of fares from the west coast. Thank you, Shirley

  20. Hi, we are looking to fly from the Bay Area (SFO, SJC, OAK) to HNL 10/25 returning 10/29, should we wait for potential price drops or buy now? Thanks!

    1. Hi Richelle.

      Currently pricing right about $500RT. Could come down down up to $100 and do suggest waiting. Availability will not be an issue.

      Aloha.

  21. I don’t think I have ever seen this before: sale prices but 7-9 hour flights, including layovers. I hate to see this because I travel to Hawaii once or twice a year and usually get a good price for a nonstop flight. Maybe those days are gone. I’m looking for LAX to Kona in October.

    1. I was able to purchase a non-stop flight out of Las Vegas to Honolulu, roundtrip was $550. That was back in May, but it is still doable!

  22. Hi we are looking to fly to Honolulu Nov 10 from Seattle and then Lihue back to Seattle November 18.

    Would appreciate advice on timing best to purchase airfares and what best rates will be. Any help is appreciated. Mahalo

    1. Hi Cathy.

      Return date will become very problematic as that is weekend/Thanksgiving holiday. Therefore suggest buying now. $595 on Hawaiian or other choices.

      Aloha.

  23. i am traveling from SLC to maui on November 3….from maui to HNL on November 10th, then back to SLC on November 11th.
    i bought my SLC to OGG for $299. i’m trying to hold out for the delta red eye non-stop flight home on November 11th (HNL to SLC). it’s about $500 for the one way right now. any suggestions how long to wait to see if it will go down? and any advise for the inter-island hopper flights?

  24. Heading to Kauai, 11/8 11/29. Would like to stop on Maui for 3 – 4 days. Prefer flying Hawaiian. Please advise as to best time to purchase tickets.

    1. Hi SM.

      You didn’t indicate where you are traveling from. Having said that your mid-week and off-season dates should be fine for better pricing. Keep watching, but there’s no need to feel pressure to buy, as availability will not become an issue.

      Aloha.

  25. Aloha! I know I missed the inter-islands sales in May, do you think there will be another sale before October 2017? Many Thanks!

  26. Looking for guidance on when to purchase tickets to Oahu for last week of August or just after Labor Day. We’ve been holding off for deals, haven’t seen any so far from RDU to Oahu.

  27. Hello, we are planning a trip to HNL from Oakland, CA for 10/11-10/18/2017. How much longer should we wait until we see the lowest prices that will likely be available? Do you think it’s possible RT prices will be under $400? Thanks so much!

    Susan

    1. Hi Susan.

      Looks like $479 currently. Could come down by as much as $75 or so and it is worth waiting for your off-season, mid-week dates. Can’t say when or for sure this will happen but again, no harm in holding off.

      Aloha.

  28. I’m looking to fly from Las Vegas to Maui 12/2-12/8. What do you think would be the best price we could get for those dates with Hawaiian Airlines and when should we book?

    1. Hi Mary.

      Until SWA joins that route, little competition and high prices. Over $700 for your dates and doubtful of it improving for Saturday/Friday travel.

      Aloha.

  29. We have our flights from the mainland and back but how about some inter-island flight information please?

  30. Traveling Nov 4-18 to Kauai first then Kona from San Diego and Phoenix. Do you think fares will go down….as they have inched up a few dollars each week recently? Alaska still seems to be the best deal with direct flights to Kauai from San Diego, and Kona back to SD.

  31. Hi!! I am looking for travel deals from SLC to Kauai in April 2018. What and when would be the best time to start looking / booking some deals. There are about 12 of us going, so I am hoping to find affordable prices, even if we need to go to Las Vegas or LA. Thank you in advance for your help!! Take care!!

    1. Hi Stefni.

      10 or more travelling together qualify for group travel rates. Check each of the airlines for that and let us know how it goes.

      Aloha.

  32. Will these fares translate into savings for someone traveling to Hawaii from the Tampa Bay (FL) area? Thank you so much for any advice or help you can give me!

    1. Hi Debbie.

      Not really. Look for a fare in the high $700’s – that is about the best you’ll find off-season.

      Aloha.

  33. I am leaving for Honolulu on July 24th from the Bay Area. I would like to fly Hawaiian. Right now their best offer is $710 RT. Do you think better offers for that time period are coming or should I make sure I have a seat now?
    Thank you for your help.

    1. Hi Kim.

      Starting at $666RT with that departure date, depending on when you return. Not likely to go down from there.

      Aloha.

      1. Thank you for your reply and advice. Also thanks for a great website that helps so many of us navigate the tricky travel waters.

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