Under the Radar: An intriguing way to fly to Hawaii

by Mohammad
a tropical garden with palm trees and a body of water

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Introducing the “Under the Radar” series. Over the coming year – I hope to write about some of my favorite sweet spots or award redemptions that, either I feel don’t get talked about enough or I myself am just discovering their utility and usefulness in my regular travels. The first one, I have toyed around with for a few years, but just never managed to find the time to fly to Hawaii… until now.

Under the Radar: An intriguing way to fly to Hawaii
Under the Radar: Awayz – the hotel award tool we’ve been waiting for?

So – with that brief intro out of the way.. let’s talk a little bit about Hawaiian Airlines shall we? And why you should pay attention to them the next time you want to fly on a lie-flat seat to the archipelago that – back when the first Europeans landed – was briefly named after the Earl of Sandwich.

Flying to Hawaii on a lie-flat Business Class seat

There are several well documented award chart sweet spots across a couple of airline loyalty programs for redeeming miles to get to Hawaii. Some of the most popular ones that come to mind include (cost for one ways):

Star Alliance programs for flights on United Airlines

  • Turkish Miles & Smiles (7.5K/12.5K in Economy/Business)
  • Singapore Kris Flyer (19.5K/39K in Economy/Business)

One World programs for flights on American Airlines

  • British Airways Avios (13.5K/~39K in Economy/Business from West Coast gateways with only occasional lie-flat service & 62K in lie-flat Business from DFW hub)

 Skyteam/ Partner programs for flights on Delta

  • Virgin Atlantic Flying Club (20K/37.5K Economy/Business for non-stops)
  • Air France/ KLM Flying Blue (17.5K/30K in Economy/Business)

The problem isn’t that there aren’t any award chart sweet spots to Hawaii… but rather the problem is, as anyone who has attempted to book a flight to Hawaii on points can attest to, finding award space.

The three US legacy carriers don’t release a ton of saver space – the lowest bucket of awards that are usually required to book flights with partner programs. Not only do they barely release saver space to partners, the award cost for the space they release for their own respective programs, is often expensive resulting in a very low value redemption of our hard-earned points.

Fly to Hawaii

Delta SkyMiles doing SkyMiles things..

Air Canada also operates a lie-flat business class option on their 787 service between Toronto and Maui (1x weekly) and Toronto and Honolulu (2x weekly) but much like the US3, space is extremely competitive and at least in my experience, have seen very little compelling redemption opportunities for either upgrade space (often no upgrade space) or Business Class (often ~200K+ Aeroplan points, if at all available).

The Hawaiian Airlines Angle

So, this is where we bring Hawaiian Airlines and their rewards program HawaiianMiles, into the discussion.

The airline has 24 A330-200’s based mainly out of Honolulu, all equipped with lie-flat business class (or First Class as they refer to it) seats that operate to various North American and international destinations. The forward cabin on the A330 has a total of 18 seats set in a 2-2-2 configuration and last I checked, is right up there alongside United Airlines in providing the most lie-flat capacity to the islands.

Fly to Hawaii

Hawaiian Airline’s lie-flat routes, FlightConnections.com

Aside from the occasional rare promotion, like the 100% transfer bonus run by Bilt Rewards a few days back, HawaiianMiles doesn’t often get talked about as much as the above programs when it comes to award bookings to Hawaii. This is partly because the same issues of not enough saver space, plague Hawaiian’s program as well, along with a not too thrilling award chart.

HawaiianMiles Award Chart

HawaiianMiles award chart is broken down across the 6 regions that it serves. The focus of this post is on Hawaii to North America, but feel free to browse the other regions as well as some of the same concepts below apply to those.

Fly to Hawaii

Hawaii – North America Award Chart

A couple of things should stand out. For starters, a First Class Saver redemption is fixed across all 3 North American regions. 40,000 miles on a redemption from the West Coast might not be anything to write home about on a regular day, but from Central and Eastern North American gateways? That’s attractive and at the same time a bit surprising – especially given that First Class Flex redemptions are charged at different premiums across those same 3 regions.

What about First Class Saver Upgrade awards and First Class Flex Upgrade awards? They too, are the same across the 3 regions. Lets take a closer look at these award options.

First Class Saver Awards

There’s no doubt that flying between New York (“JFK”) and Boston (“BOS”) for 40,000 miles on a lie-flat is a great deal considering this is Hawaii we’re talking about. How’s award space though? Well – it’s not great but it does occasionally pop up. Availability can probably be as challenging as a lot of the sweet spots highlighted above, especially from the East Coast. Working in Hawaiian’s favor though, is that there aren’t nearly as many eyeballs on the space – so if space is released during a period of interest, as long as you’re diligently checking, you should have decent odds of booking it. Add to that, Hawaiian Airlines First Class space is supported by Expert Flyer so can be a good option to set alerts on your dates of interest.

In fact, all of Hawaiian’s Saver, Flex, Saver Upgrade and Flex Upgrade space can be searched using Expert Flyer. A sample search below shows an upcoming date where all 4 types of awards are available. It’s interesting to note that whilst Flex and Flex Upgrade have the same code (i.e. when one is available, so is the other), Saver and Saver Upgrade do not.

Fly to Hawaii

Hawaiian Airlines First Class Saver (D), Saver Upgrade (A Code) & Flex Award/Upgrade (P Code) space

Contrast this – a comparative route like YYZ-HNL/OGG, you’re talking 200,000 Aeroplan points usually.. for pretty much most of the calendar. I would note that I’ve often seen Saver space becoming available close-in on a few occasions, though it has not been particularly predictable.

On a personal front, I recently swapped out a flight back from Maui to Ottawa (via Vancouver) for 63,000 Aeroplan points for the first in Economy (latitude and waitlisted)/ second leg in Business, for a Honolulu to JFK direct flight on a Hawaiian Saver award. I’m glad to report that I heeded my own advice from Confession Corner and was able to cancel the Aeroplan award ticket without penalty 😊, replacing it with an HawaiianMiles award for 40,000 points per person Saver award for two people, transferred from my US Amex Membership Rewards account. Follow along on IG if you want live updates on how the experience stacks up.

Fly to Hawaii

Even though there is the occasional smattering of Saver space over the next 30 days, there continues to be large swaths of the calendar that lay bare – cue Saver and Flex Upgrade space to the rescue…

Saver/Flex Upgrade Awards

This is where the program gets interesting. With Hawaiian Airlines, any ticket purchase can be upgraded for a fixed number of points provided there is either type of upgrade space available – and I really do mean any ticket – even Basic Economy (EDIT: As of June 2023, reader Jimmy was advised by multiple HA agents that basic economy can not be upgraded. Please see comments box at the end of the post for more details).

Typically to upgrade a ticket, you need to call in after buying your Economy ticket. It’s advised to book straight on Hawaiian’s website instead of with an Online Travel Agency as that can present some (ultimately surmountable) challenges when processing an upgrade with a phone agent.

Since Saver awards are already so attractively priced at 40,000 miles for First Class awards, it will seldom make sense to upgrade to First Class by paying the Saver Upgrade amount when Saver space is available.

With that in mind, lets take a look at the below example for a flight back from Hawaii right after the Labor Day weekend – a time where award space is usually quite tight. A Basic Economy ticket between HNL and JFK comes to $519.

Fly to Hawaii


The corresponding date search on Expert Flyer shows that 7 First Class Flex Upgrades are available – meaning you can book your family of up to 7 people for $519 + 50,000 HawaiianMiles for a direct lie-flat seat all the way to the East Coast.

Fly to Hawaii

Flex Upgrade space for up to 7


In the same example, if you are flexible with dates- you might be able to score an even better deal. Leaving on Tuesday Sept 5th, the cost of a Basic Economy is still the same $519 as above, however upgrade space shows up as follows:

a screenshot of a computer

Flex Upgrade and Saver Upgrade for up to 7 people

Leaving a day later means you’d still be able to fly your family of 7 back on the HNK-JFK route in first class, but for $519 + 25,000 HawaiianMiles – for a seat going for $2,776 on the same day. Not only is the price compelling – but so are the number of seats available for upgrade. Also unlike the Saver space – you can often find availability scattered around the calendar for both the long haul routes to New York and Boston, but also to the West Coast gateways… even to some of the international destinations across the Pacific.

Why should you keep Hawaiian Airlines in mind

While Hawaiian Airlines offers a very comfortable way to fly directly to the East Coast, amongst other destinations, in a lie-flat configuration – it isn’t quite the “cutting edge” hard product. There’s some excitement on that front as well. Back in 2018, Hawaiian had placed a firm order for 10x 787-9 Dreamliner’s with deliveries expected to begin in 2021. Unfortunately, with all the issue’s Boeing had with delivering the Dreamliner – I’m sure COVID didn’t help – there has been an expected delay to the schedule.

Latest news however is more encouraging as the airlines added another 2x 787-9’s to their initial order and the airlines is expected to receive its first 787-9 by the end of 2023 with a gradual delivery of 2-3 planes a year until order completion. I’m sure the schedule will be fluid – however the reason this news is exciting is that with the new planes, Hawaiian will be introducing a brand new hard product in the form of 34 Adient Ascent seats (up from current capacity of 18 first class seats per plane).  With doors to boot for those who might be wondering.

a bed in a plane

Once delivered, Hawaiian’s First Class seat will be the most comfortable way to fly there

Expectations are that the first markets to get the 787-9’s will be the New York and Boston routes – making an even stronger case for looking to book the carrier via one of the ways discussed above.

How to earn HawaiianMiles

To quickly recap the different methods of earning Hawaiian miles that I’m aware of currently:

  • Transfer partner with US American Express Membership Rewards and Bilt Rewards (1:1 ratio)
  • Transfer partner with Marriott Bonvoy (3:1 ratio or blocks of 60,000:25,000 for a better ratio)
  • Purchase for 3 cents a points from Hawaiian’s website. You need to have activity before purchasing, but transferring in a small number of points would be an example of qualifying activity.

Amex does tend to have ~2 transfer bonuses a year with 20-25% bonus miles to Hawaiian. Bilt Rewards ran a really good 100% transfer bonus for the first time on Feb 1 of this year. Hopefully they do it again at a time when I’ve managed to build up a better Bilt Rewards balance!

Final Word

Hawaii is a dream destination for many and Hawaiian Airlines provides a competitive product covering a robust network. Yet – it doesn’t get talked often enough about the value it brings. Personally I’m excited to have booked one of the above sweet spots for a flight to JFK  in a couple of days and hope that others can also benefit from this. Let me know below what you think of Hawaiian – or any pro’s or con’s I may have missed.


J August 12, 2023 - 1:00 pm

Can I book saver main cabin award flights with points and then upgrade those tickets with points, assuming upgrades are available? Or would those saver award flights be considered restricted and not upgradable?

Mohammad August 12, 2023 - 2:28 pm

I’m not sure… I had not thought of that. So I assume you would do this in a scenario where saver business is not available.. in any case – it might be worthwhile checking with one of their chat agents if award redemptions on main cabin awards are eligible for further points upgrade. My guess – and it is only a guess – is that it might be eligible. I say this because award redemptions are eligible for cash upgrades based on HA’s website so suspect it might be the same. Its a good question though – and I’ll be sure to ask it the next time I connect with an agent.

Amy July 26, 2023 - 9:49 am

Hello–I did this upgrade trick last night and it worked great. I didn’t even call, just used the chat feature as I booked my flight online. The chat agent “Cassandra” told me to book the Main Cabin and then let her know when it was booked and she processed the upgrade. I simply followed her instructions. I didn’t ask to book basic. Anyhow, super happy it worked. Can’t wait for my family of 4 to get to try first class. Figured for an 11 hour flight from Boston it was worth the 50k points per person to upgrade. I already had 77k Hawaiian Miles so I only had to transfer 123,000 Amex MRs. Thanks again!

Mohammad July 26, 2023 - 11:27 am

Hi Amy- thanks for sharing your successful experience! I’m excited for you!

You’ll really enjoy the flight- it was well worth it. Having done the HNL-JFK redeye- I got solid sleep in and arrived in JFK early morning ready to have a full and productive day. You didn’t mention when your flight is- but let us know how your experience goes!

Jimmy N June 26, 2023 - 2:21 pm

Want to call out that this bit is *not* accurate.
“This is where the program gets interesting. With Hawaiian Airlines, any ticket purchase can be upgraded for a fixed number of points provided there is either type of upgrade space available – and I really do mean any ticket – even Basic Economy.”

I tried this a few days ago and multiple HA agents (on the phone) informed me that upgrades from Basic Economy are *not* allowed per the terms of that fare class. I needed to cancel and rebook Main Cabin in order to upgrade…

Otherwise, this article has been *awesome* for guiding me through my first FC redemption ever! Thank you!

Mohammad June 26, 2023 - 2:44 pm

Hi Jimmy – thanks for this.
This is interesting indeed.. I had talked to a HA agent about this in theory and the first one didnt sound like they knew what they were talking about, however on a subsequent call they said the Basic Economy ticket was eligible.

The only reason I tried again was because there was a corroborating dp of someone actually having done this on Flyertalk – otherwise I wouldn’t have bothered trying to ask the question again. In any case – your experience is a more recent one, and I’ll put an note in the post warning of your experience – and hopefully soon, I can try calling into Hawaiian and try to get to the bottom of this.

Other than that – I’m so glad you found it useful and were able to use this to make the actual redemption!

Sheri March 11, 2023 - 7:36 pm

Does the upgrade availability show up on Hawaiian’s website? Is there any other wsyllay to look up that availability without having to go through a paid subscription?

Mohammad March 11, 2023 - 8:08 pm

Hi Sheri – I mentioned in the article that Flex/ Flex upgrade space have the same class code, whilst saver space and saver upgrade space do not. So with this in mind, I would assume if Hawaiian’s website shows Flex space available on points, then the flex upgrade space will definitely be available as well. Unfortunately – I don’t think this would be an accurate way to determine saver/ saver upgrade space.
But Expert flyer often has some free trials available – currently you have a 5 day free trial you could get to run your search results – just remember to cancel before the trial runs out. In future you could always sign up with another family members email to run a different batch of searches for another trip if needed.

Pascale February 13, 2023 - 7:35 am

Very interesting, thank you.
Keep the sweet spots reviews coming, I love it!

Mohammad February 13, 2023 - 2:03 pm

Glad you found it interesting! Hope to include more in future!


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