This Cheapest Time to Fly to Hawaii features our six-article guide, just updated. Read our new tips on Hawaii vacation deals, the best and worst dates to travel in 2019, when to buy, and what prices to expect during all seasons, including holidays.
This, one of our most popular posts ever, has been read millions of times and has nearly 5 thousand comments and over 61,000 Facebook Likes. You’ll find questions and answers helpful to finding Hawaii vacation deals! Then add your comments and questions.
We are all anxiously awaiting more routes from Southwest Airlines and it could come at any time. Read all the details on Southwest Hawaii flights.
Cheapest Time to Fly to Hawaii – What to Expect Throughout 2019.
Earlier this year we saw Hawaii flights on both United and Alaska for just $99 each way. Southwest outdid that by far with mainland to Hawaii introductory fares of just $49 each way. It doesn’t get any better than that! These could return again so be sure to subscribe to our free email updates and be first to get Hawaii deals.
Great News for Value Hawaii vacations!
Flights to Hawaii remain at inflation adjusted low prices and this is only going to get better – probably a lot better. That’s good news for 2019 Hawaii vacations. Recent and upcoming competition and strong discounting on many routes result in cheaper than expected flights to Hawaii.
The two largest Hawaii air markets – Southern California and Northern California, continue to see improving sale pricing as a shake up in competition is occurring. These will only improve throughout 2019. Since California flights to Hawaii will be highly impacted by Southwest, they should have the best airfares going forward.
Seattle and Portland have have had increased competition as Delta competes head on with Alaska Airlines from the Pacific Northwest. Seattle has benefited most to date with excellent prices on both Delta and United. This is also having a positive effect on the price of flights to Hawaii from Portland.
San Diego and Sacramento saw favorable improvements in prices on flights to Hawaii and there may be new flights from those cities this year. These cities will have flights from Southwest!
Start your Hawaii vacation planning now with our helpful guides below.
Six Articles To Help You Find Hawaii Deals
Cheapest Cities for Hawaii Flights and Costs
Cheap Flights to Hawaii | When to Buy With Southwest Hawaii Here
Flights to Hawaii – Updated Costs by Region 2019
Best Airlines for Flights to Hawaii Updated
Best Time to Visit for Hawaii Deals in 2019
Questions and Comments.
We continue to update the information contained here very frequently.
You’ll never miss a deal when you subscribe to our free deal alert emails.
We look forward to your comments and questions. We try our best to respond to most comments individually and timely. If you read the comments, we have already answered many of the most asked questions. And if you would like to respond to others’ comments and questions, we encourage that too.
E komo mai (Welcome). Mahalo and A Hui Hou!
Miguel says
I am planning a trip to Maui from Sacramento Feb 20 through March 1 2020. Will or when will HA or Alaska have there sales for winter or fall? Airfare is around $577 now, should I wait until a couple of months before flights or book now? thanks in advance
Beat of Hawaii says
Hi Miguel.
Perhaps from mid-summer to fall for winter sales. Looks like target price for your dates and days of week will be about $450. Could even be better when SW starts flying, if that happens by then.
Aloha.
Tess says
Will HA have 4th of july sale? I am trying to go in December and want to know a good time to buy.
Colin says
Hi BoH,
Looking for your guidance to plan a trip for August 2020.
When in general do the first sales for summer normally take place? Is it when the flights are released, ie. 11/10 months in advance like the major international airlines?
Or even, waiting for black friday?
Do hotels tend to offer deals for Hawaii around black Friday too?
We would be travelling from west coast to Oahu with perhaps a 2nd week on Big Island.
Thanks for your words of wisdom and guidance!
Colin (UK)
Note: Only other trip to the Hawaiian islands was during Hurricane Lane (Aug 22-29 2019) but its still our best destination and holiday ever. Loved it and the people and looking forward to seeing the sun next time and some of the sites that were unfortunately closed.
Beat of Hawaii says
Hi Colin.
Glad you’re coming back. For 2nd week of August and beyond, you’re in low season. Best prices for that time will probably be available in May to June. Black Friday won’t help. If you’re 1st week of August, that is high season, and that would typically be best 11 months out. Only hestitation on that is that Southwest has largely postponed 2019 rollout to 2020, and that could have benefit for summer 2020 prices. That part is not possible to call.
Aloha.
Emily G. says
Looking at flights from ATL to OGG around 9/21-9/29. Not sure if these flights around $715 are good or if I should wait. What do you think, we have to buy 4 seats so we are trying to go budget friendly.
Bev S says
Could you please let me know what you think the minimum reasonable connection is at HNL? We are landing from Atlanta on Delta at 2:20 p.m., and would like to take Southwest to KOA, but our choices are either a 3:40 or 8:25 p.m. departure. One seems pretty close, the other seems like a really long wait. I would appreciate any advice, we are so excited about our first trip to Hawaii. Thank you for your help.
Beat of Hawaii says
Hi Bev.
Would suggest a minimum of two hours. You didn’t mention luggage, but if it is checked, that adds to the complexity since you’ll be retrieving it and rechecking it, plus security in Honolulu.
Aloha.
Chris says
We are looking at flying from OKC to OGG August 30-September 6. Do you expect any more late summer early fall deals coming out or should we go ahead and book?
Glenn says
I am planning to have my wedding the weekend before Thanksgiving. Flights right now are about $830 nonstop round trip from NYC. I missed the sale a couple months back. Should I book now or should I expect another price drop soon?
robert says
please i have a dumb question…if on the flight i am on as i am getting on has empty first class seats..do they sell the seats at a discount..and if so what can i expect would be a good discount
Beat of Hawaii says
Hi Robert.
Usually at the point of walking on the plane, it is too late. The point at which you can expect upgrade offers to be available is at the 24 hour online check-in. To/from Hawaii, you might expect cost to upgrade to first class of anywhere from $150 to $500 or so. To premium economy, starting at under $100.
Aloha.
Carol C says
Hello,
Thanks again for your help! What are you thoughts about OAK to OGG September 22nd or 23rd? I can use San Jose if that helps at all.
Mahalo Nui!
Beat of Hawaii says
Hi Carol.
There are $350 RT flights using either of those two departure dates. Same for SJC. Gut feeling is those could improve by $50 or so if you wait. Availability should not be an issue so log as return isn’t a Saturday.
Aloha.
Joann W. says
Would like to book for an exuded trip in the next 16 months.Possible family members added. Are there discounts for groups?
Brooke says
Hi there, We are looking to travel the last week of September for our 10 year anniversary. I’ve been watching the rates but they are all around 5oo+… do you think rates will improve? (from LAX to maui ((OGG)) thanks so much for your feedback!
Beat of Hawaii says
Hi Brooke.
If you are flexible and can do mid-week travel, it seems you can do better. Suggest a target price of about $400 or so, and that should occur by July. Good idea to wait.
Aloha.
Brooke says
We are looking to travel the last week of September for our 10 year anniversary. I’ve been watching the rates but they are all around 5oo+… will rates improve? (from lax to maui)