Hawaiian Airlines Deals

2019 Predictions | When Will Southwest Hawaii Flights Start, Pricing & More!

Exciting times. As 2018 draws to a rapid conclusion, it’s time to review 2019 predictions.

Continue reading

Get Breaking Hawaii Travel News

Please enable JavaScript in your browser to complete this form.

297 thoughts on “2019 Predictions | When Will Southwest Hawaii Flights Start, Pricing & More!”

  1. We’re flying June 20 or 21, 2019 from Seattle to Honolulu for 7-8 days. Right now cheapest nonstop roundtrip flights are on Delta & Hawaiian for $700, Alaska $750. Will this price go down as we get closer to end of 2018? These same flights in 2017 were $450 roundtrip.
    Mahalo – Tom S.

  2. Hi,
    We are headed to Maui 2/9-16 from Oakland CA. Tickets are looking to be around $600 right now. Should we buy now or do you think they will go down over the next month? I am using miles for one ticket, and a companion fare for a second, but we will be paying full price for 2 additional tickets.

    Thank you!
    Valerie

    1. Hi Valerie.

      Currently $441RT on Hawaiian. Very well may improve with SWA being on board. But since you are flying on Saturdays that is less certain. What to do depends on how well you like waiting and not knowing.

      Aloha.

  3. Hi, first of all love the site, thanks for the work you do!

    We want to fly Denver to Honolulu return April 1-8 – we chose weekdays to get the best fares.

    Has to be non-stop as we’ll have 2 toddlers in tow – best option is looking United currently at around $750 per person.

    Should I be waiting to book these…? Was hoping to get something at the 400-500 range, but not sure if flights as far as Denver are often discounted.

    Thank you!

    1. Hi Doug.

      Thank you!

      It is a monopoly on that route at this moment. Not out of the question that HA would get on that route, but that’s only a maybe, and then if it happens, when.

      Also, although weekdays, that helps, but it is still spring break.

      Gut call is to buy at $750.

      Aloha.

  4. We are flying from Sioux Falls Sd to Kona on the big island on Jan 23 through Jan 30th 2019. When is a good time to purchase our tickets?

  5. I have a vacation planned for March 8, 2019 – March 15, 2019 when is the best time to buy my tickets. I can leave from any southern California cities (LA, San Diego, Long Beach, Ontario)and going to Honolulu.

    1. Hi Sandy.

      San Diego will probably be cheapest. Fridays in spring break aren’t likely to ever get cheap. Looks like about $600 now. Maybe you’ll be able to get it down to $500 after Southwest enters, but not entirely sure on that. They are going to try to make money too.

      Aloha.

    2. My wife and I have booked a condo in LIH Kauhi and need to depart from SLC April 3 and return April 16, 2019. When is the best time to purchase tickets? Will the price go down this fall or laterin the year?

  6. Any prediction on cost for CLE to LIH October 31 and to HNL November 4 and HNL to CLE November 10. First class!

  7. Hi, my husband and I would love a trip to Hawaii and have decided to go in 2019, probably for 2 weeks. We are wide open as far as dates are concerned and really not sure which island to fly to. We love hiking, and not crazy about being around tons of people while on the beach. We are open for any suggestions, best times etc. We will fly out of the Washington, DC/Baltimore airports. Your advise and suggestions would be greatly appreciated!!

  8. Hi, I’m finding flights from Salt Lake City to Kauai departing on 9/29 and returning on 10/6 starting around $650 round trip. What would you anticipate the best price to be and when is the best time to buy tickets? Thank you so much for your help.

    1. Hi Mark.

      Because you’re traveling on Saturdays, it may not improve at all. Even just switching to Fridays will save $100, if that works for you.

      Aloha.

  9. We are planning to go to South Kona the week of MLK holiday in January, somewhat flexible dates are 1/21-1/28. We are flying OAK to KOA. Rates now are $436. We’ve been watching them for awhile and they seem to be creeping up, and can’t find nonstop anymore. Last year we snagged great fares for the $350 for the same trip. It seems unlikely we will find a great deal like last year. What do you think?

  10. My husband and I have a confirmed timeshare booked in Maui for April 19, 2019 returning on May 3, 2019. Preferred round trip is from Sacramento to Maui, first class. When should we book tickets and what airlines should we use. Thanks!
    CK

    1. Hi Carmen.

      If you want nonstop you have only one choice, Alaska. Otherwise airline is a personal decision. Currently $1,700 round trip. Not sure it will go down.

      Aloha.

  11. The cheapest airfare going from SFO to HNL on 12/23/18 and return from OGG to SFO on 1/5/19 I can find now is around $1,105. I know this is obviously a peak season. Do you think I should wait and is there any possibility the price will go down a bit?

    Your advice is very appreciated!
    Annie

    1. Hi Annie.

      Equally likely that price will come down, will go up, or will have no availability. Thus it comes down to your determination for this trip. If it is set on those exact dates and you are going, suggest paying up now. IF you have any flexibility at all, even a one day change could save hundreds (12/24-1/6).

      Aloha.

  12. Flying from Seattle to Maui 10/23/18-10/30/18. Hawaiian has rate of $476 today. Do you anticipate lower fares before then?

  13. Flying to Maui from DC area on 12/14 and heading back from Honolulu on 12/30. Flight prices keep going up and the layovers on the way home are absurd. Costs about $1250. Do I book now or is there hope of prices going down? Thanks!!

    1. Hi Emily.

      Without changing dates even by one day the chances of improvement are slim to none.

      Aloha.

  14. Hello! We have accommodations booked 12/5-12/15 on Maui and are now watching airfares. Either ORD/MKE/ATW – OGG with a redeye departing 12/4 a definite possibility- trying for early arrival. We have traveled these dates in the past to OGG and were lucky with the 44-30 day out purchase time frame. Should we take the same approach this time or book now? Shooting for the 600-700 range. Love the Island and cannot wait to be there again. Mahalo in advance- Love the website!

    1. Hi Nick.

      Thank you. So about $800 right now on multiple carriers from MSP with good connection. Your Saturday in high season return date will block any possibility of great fare obviously. Better price would require return by 12/13 and if you go that way then do wait. Lacking that flexibility, however, suggest booking now at $800 as it isn’t likely to improve by much if at all.

      Aloha.

  15. Any suggestions for when to book for a Dec 6-15 flight. Some flexibility, but it’s the Honolulu marathon, so I’d like to be there a few days earlier to relax, etc. It’s from MKE, so I’m not expecting these to be cheap, but is $850 absurd?

  16. Aloha!

    My family is traveling to Kauai from PDX or Seattle from March 25 – April 4, 2019. We’re using miles with Alaska for some of the tickets but still have to purchase some tickets. I’m concerned that with fuel prices rising and going on Spring Break, we should book sooner rather than later. When would you advise to book?

    Mahalo and Aloha!

    Justin D.

    1. Hi Justin.

      Spring break, unlike Xmas and Thanksgiving, is a moving target. So it is harder to accurately predict until it gets closer. It does look to be expensive, running about $700 RT on Alaska. Unless you have date flexibility, not sure that will improve by waiting.

      Aloha.

  17. Aloha!

    We plan to fly PDX/HNL roundtrip March 29-April 6, 2019. When is the best time to book?

    Mahalo!

    1. Hi Wendy.

      Looks very expensive during those spring break Fridays and Saturdays. Probably won’t go down so you might just need to pay up. If you’re flexible about coming or not, and about days of travel, then you might do better. Otherwise not.

      Aloha.

  18. I left this on another thread but don’t think it was an updated article.

    We are traveling from Seattle to Kauai. We are departing Seattle on 9/13 (flight already booked as a oneway to snag a $218 deal) but I’ve been watching flights for our return on 9/20. I haven’t seen the return flight any lower than $360 for nonstop that isn’t a red eye. Do you think $360 is as low as it will go?

  19. We’re a family of 11 flying to Maui for Jan. 19-26, 2019.
    When is the best time to book our flights? Last time we traveled to Kauai and really enjoyed flying Hawaiian Airlines.
    Thanks!

    1. Hi Lisa.

      Do check with multiple airlines regarding group rates (10 or more traveling together). Your Saturdays are going to be a problem in terms of best rates. Can’t provide target price as you didn’t say where you are traveling from.

      Aloha.

  20. We are traveling from Bay Area (Oakland or San Jose) on 4/13/19 and returning on 4/27/19. Could leave a day earlier or return a day later. We are a family of 4 and have 2 free companion tickets on Alaska Airlines. Tickets have not gone on sale yet, but will soon. Tickets seem to be over $1200 round trip or more. What are the chances of these going down?

  21. Hi. My wife, son and I are flying to Honolulu 12/30, returning 1/4/19. Right now, nonstop flights are around $1k each roundtrip. Will prices normally get lower as we get closer to the dates, or will they go up? I know you can’t see the future, but I imagine you’re familiar with the trend… I also just subscribed to both Hawaiian and Alaska Airlines credit cards, both of which offer a free companion ticket after spending $1k in 3 months. However, I wouldn’t be able to book until 3 months from now. So is it worth waiting until August – or even later – or should I book asap?

  22. Hi, I have trip planned to Kauai for July 21-28, 2018. I know if I fly in on the 20th I can save a little money and pay for one night in hotel before checking in to resort. Last week I saw prices for low $3000 for 4 leaving from Miami (MIA), now they are trending high $4000. Will they come back down some? Should I wait? Any search suggestions are welcome.

    Thanks in advance for your advice.

    Chris

    1. Hi Chris.

      Summer prices are more unpredictable, so it could come down, but it could just as easily go up. Best we found was $996 on American 7/21-7/29. Fast connection. Otherwise $1,224 for your dates on same flights.

      Aloha.

  23. My husband and I want to take our 2 teens to Honolulu to celebrate their high school graduation. We will be flying from San Diego June 17-June 23, 2018. It is now May 8th and I just got the funds for the trip. The tickets seem to be ranging from 760 on up. Should I buy now or wait a little but?
    Mahalo!
    Martha

    1. Hi Martha.

      As of this moment, over $1,000 on your dates. If you come back instead on 22nd, then $884 or 24th $935. Probably won’t improve unless at very last minute. Reason being that your dates are highest seasonal ones including weekend travel. If you want to do mid-week, like 20-27 June, then prices are just under $700RT.

      Aloha.

  24. Hello!

    I just found your site. This week, I booked a condo in Maui for Saturday, 3-9-19 to Friday, 3-15-19. Great deal. Then I checked airfare. Normally fly either American or Southwest; I about died when I saw AA’s fare. For the 4 of us, we’re looking at a minimum of $5061 right now out of DFW. I found a fare with 2 stops on United for $3509 r/t for 4, but don’t know if I should go for that or not, especially with some of the feedback I’ve gotten about their on-time record and customer service.

    So my question is…if I wait, am I going to end up paying $6k or more for these 4 tickets? I was so excited for this trip, but I didn’t guess that the airfare was going to be twice the cost of lodging (I did know it would be more than we’re used to paying for domestic flights).

    Thanks in advance for your time!

    1. Hi Kerri.

      We don’t know yet just how 2019 spring break peak travel dates will hit and airlines will keep adjusting prices based on spring break demand. You may be in peak dates or just before them, but at this point the airlines think you’re in them. Thus prices for your dates are much higher than the previous week.

      What we find at the moment is range of $700 to $1300, mostly depending on duration and number of connections. There is probably nothing better or worse as far as United vs. American goes.

      Not sure if your dates (which are expensive Saturday departure and Friday return) will improve. Somewhat doubtful.

      Aloha.

  25. Need to find best deal from SC to HI. June 12 or around there for 2 is it best to find flight to west coast and then from there to island any help is appreciated. I want to go visit son for 8 days and daughter for 2 weeks.

  26. Going with a tour to east coast, need to fly from Honolulu to JFK on Oct. 4; return Oct 21. Would love to fly 1st class (or extra comfort) if possible using all Hwn Miles OR Miles and dollars if have to. When do you recommend placing reservations? Seems award/all miles seats are hard to get.

  27. Hi! I am noticing everybody commenting seems to be from the west coast but we are coming from Chicago and wondering what airline is our best option for flying to Honolulu April 13th coming back April 20th, 2019.

  28. Hi, will need to book a flight from Bay Area to Honolulu for mid July however will probably need to wait for some funds to come in so may not book until mid June. Am I likely to see much higher prices by waiting to book?

  29. Looking for advice on flights from MSP to HNL for a group of 8. Dates ~12.26-1. 5. Airfares are really expensive. Any chance of them coming down?

  30. Looking to fly to Honolulu from 12/22-12/29/18. Currently round trip prices are from $1100 to $1300 out of SFO!! When is a good time to buy? And please tell me they will get lower. I can fly cheaper to almost anywhere else on the planet. ugh.

    1. Hi Julia.

      Two of the most expensive travel days of year. $938 on Delta is least expensive. If those are your set dates, then suspect you’ll need to pay up. And better soon than later as it appears to be very tight availability.

      Aloha.

  31. We are flying to Kona from Phoenix on Aug 21st. We are then flying to Maui on the 26th and returning to Phoenix on Sept 7th. The options leaving on Aug 21st seem to be similar pricing on AA, Alaska and Hawaiian around $352 ow. We prefer to take the daytime flight back from Maui on Sept 7th on Hawaiian air and that flight is $378. I have been checking daily and the rates seem to keep going up on Hawaiian air. Their pricing fluctuates even throughout the day. Not sure if I should lock in flights now or wait to see if there may be a sale.

    Thanks

    1. Hi Allison.

      There is the potential for the transpacific segments to be as low as about $450 RT. Plus inter-island. Might happen, might not. If so, probably in the next 45 days or so.

      Availability should remain good if you choose to wait and have some flexibility for time of day/day of week. Friday return could be problematic.

      Aloha.

  32. Our family of 3 is looking to travel from Seattle to Hononlulu round trip from 9/6/18-9/15/18. It looks like round trip non-stop is at about $577 a ticket right now. I am thinking that is a pretty good price, but not sure.

    Thank you!

    1. Hi Brett.

      Got your 2 comments – thanks for clarifying it was from Seattle. Might not come down much due to your Saturday return. If you are willing to take a chance and wait up to a few months, however, there’s room for up to $75 savings even with Saturday. Depends on your comfort level with the unknown. Airlines count on that. 🙂

      Aloha.

  33. I am going to Kauai with my family from July 18-25. We are traveling from the Bay Area (SFO, OAK,or SMF). The rest of my family purchased their tickets months ago, but I have waited. Prices are pretty high right now, do you think there will be any sales for July travel?

    Thanks!

  34. Hi there, We are a family of 4 looking to purchase tickets flying out of Seattle to Lihue 10/28-11/13 2018. Finding Hawaiian to be what we would like to fly and around $530/ticket. Should we wait a bit to see if it goes down or buy now due to the Sunday take off date?
    Thank you for your time!! Very helpful!

    1. Hi Shannon.

      $444 on Hawaiian one-stop. United, Delta and Alaska are even less money. Could get lower but might not be worth waiting and trying to find something better. Suggest buying.

      Aloha.

  35. Looking at flights for Thanksgiving week from SF area during prime time aka sat – sun… currently looking at ~$1500 on Alaska (preferred airline due to status), which seems high. Do you anticipate better deals? Thanks!

    1. Hi Greg.

      Prices are $1,300+. It could come down in a few month, but it could just as easily be sold out. Looks tight. If you’re okay not coming if it doesn’t work out, then definitely wait and see. Otherwise, there’s nothing to suggest other than paying up or changing dates. If you can do Sunday to Monday, the fare on Hawaiian drops to $886 RT out of OAK or a few dollars more from SFO.

      Aloha.

  36. We booked a townhome on the Big Island for February 28, 2019 – March 15, 2019. We have the flexibility of leaving on the 14th since Thursdays tend to be cheaper. My sister’s family is going to try and come so we needed to go during spring break which I’m sure will be higher. When should we look at booking our flights? They are quite high right now and not very good options. Mahalo!

    1. Hi Melanie.

      On your dates $941. If you return a day earlier, same flights are $808. You can leave a day earlier as well if you prefer. That’s on American with a good connection.

      Aloha.

  37. We are looking for the best price on a roundtrip airfare between June – December (10-14 day stay) flying into ITO/KOA From LAX for my adult nephew who would have the cheapest rate?
    Thank you very much

    1. Hi Janet.

      Best thing to do is watch for sales coming up for fall season (starting mid-August). Otherwise currently in high $500’s at the moment. Do you get our email updates?

      Aloha.

  38. Our family of 5 is going to Maui the week of October 30th-November the 6th. We are flying out of Portland Oregon. I’m currently seeing non stop flights on Hawaiian airlines for $457 but I’m wondering if we should hold off buying in hopes prices will go down or should we book now?

    Thanks,

    1. Hi Pam.

      As of just now, $410 on Hawaiian nonstop. Good price for that far out. Price could drop to about $350 or perhaps slightly lower, if you’d rather wait a few months and see.

      Aloha.

  39. We are soon to be frequent visitors to Oahu, my daughter will be attending UHMaoa in the fall. Looking to bring her out August 14 from Lax area, willing to leave from any cheaper airport though. I will return on the 19th, should I book now or wait? Also, should I be booking her trip home for Christmas now too? I just signed up to receive your emails, so glad I found this site! Thanks for any advise you can give me!
    Mahalo! Cathy

    1. Hi Cathy.

      Looks like about $550 if you book now. Might improve in next month or two, although your Sunday return could be a problem in that regard. Christmas should be booked far in advance.

      Aloha.

Comments are closed.

Scroll to Top