Redeeming Miles To Hawaii Can Be Tough

Filed Under: Advice, Awards

Reader CLH posted in the “Ask Lucky” forum asking for help planning a trip to Hawaii. The full conversation is rather lengthy, but here are the relevant excerpts:

…I am trying to book DFW-LIH for next summer – exact dates July 20-30 (or 18-28 or 19-29). BA website ALWAYS tells me there is no availability for any dates around what I have selected (not just for this proposed trip but every time I search). I actually called BA directly because I thought there was a glitch in the system and surely there must be some availability somehow somewhere. But they said, nope, the website is correct and there is no availability because they can only access a couple of AA reward seats and the only way to get those seats is to watch constantly and book as soon as I see them appear. This just made me wonder about the potential to use Avios on any partner airline.

I checked other airlines and found availability on United/American/Delta/Virgin, but I could see no way to piece together a first/biz class honeymoon trip for my sister & her fiancé. I have pretty much resigned myself to getting the Delta economy seats for them, but thought I might check here to see if there’s something I’m overlooking. I feel like I must be doing something wrong in not being able to use 450k+ points to buy 2 tickets.

What am I doing wrong here? Any advice is much appreciated.

P.S. Now doubly frustrated as I have approximately 200,000 Membership Rewards points, plus 200,000 BA Avios and about 50,000 Chase UR points. Not enough MR points to buy first class on any other airline. My only option appears to be using 160k Membership Rewards points to book sister & BIL in economy on Delta. Just really bummed because I thought I had a lot of miles and I would be able to give them first class tix.

Award availability to Hawaii is generally disappointing, and I can absolutely relate to how frustrating it can be to redeem miles to Hawaii — especially the smaller islands.

So let’s unpack this a bit. I’m going to write this out “live” as though I were researching space for a client — hopefully seeing the process helps in booking your own awards, and ideally we’ll find space for CLH’s sister.

Where to start

Firstly, we know we’re going to Hawaii, and we have specific dates we want to travel. This makes things a bit more complicated, but there are ways to expand the options a bit, such as:

  • Booking awards to Honolulu or Maui, and paying for the connecting flight to Kauai
  • Paying for a positioning flight from Dallas to the West Coast

Either of these alternatives will expand options dramatically, so are probably worth the extra cost. Let’s see what we can find otherwise though.

Going back to the other week when I talked about how to decide which miles to use, the next step is to think about which award represents the best value:


Lihue has pretty limited service, so we only have the following carriers and routes to explore:

  • Alaska Airlines | Oakland, San Diego, San Jose, Seattle
  • American Airlines | Los Angeles
  • Delta Air Lines | Los Angeles
  • Hawaiian Airlines | Los Angeles
  • US Airways | Phoenix

So let’s walk through the potential award options to see the comparative values.

Don’t assume British Airways is best

Now, CLH defaulted to thinking Avios were the best option here, and I understand that thought process. British Airways awards to Hawaii get a lot of screen time, and Avios are easy to accrue.

Avios also offer a fantastic value to Hawaii in economy, and on direct flights. A flight from Los Angeles to Lihue on either American or Alaska would be just 12,500 miles one-way, which is great!

When it gets to premium cabins, however, the value drops dramatically. British Airways charges at least double Avios for business class, and at least triple for first class. Because of how partner flights are coded, you’d pay 50,000 Avios for a one-way first class flight between Los Angeles and Lihue. 

Beyond that, because British Airways has a distance-based award chart that charges by segment, you’d pay for the Dallas > Los Angeles flight separately. This would be another 10,000 miles in economy, or 40,000 in business.

So you’re looking at somewhere between 60,000-90,000 Avios per person, each way. That’s just a downright excessive number of miles, in my opinion.

What other options are there?

Of the carriers that fly directly to Lihue, each has a few options for redeeming miles.

Alaska Airlines

  • 60,000 Korean Air SkyPass miles round-trip
  • 37,500 American AAdvantage miles one-way
  • 40,000 Alaska MileagePlan miles one-way
  • 40,000 Delta SkyMiles one-way
  • 50,000 British Airways Avios one-way on nonstops from the West Coast

American Airlines/US Airways

  • 37,500 American AAdvantage miles one-way
  • 47,500 Alaska MileagePlan Miles one-way
  • 50,000 British Airways Avios one-way on nonstops from the West Coast

Delta Air Lines*

  • 45,000 Korean Air SkyPass miles round-trip
  • 60,000 Alitalia Millemiglia miles round-trip
  • 80,000 Alaska MileagePlan Miles round-trip
  • “Some” Delta SkyMiles depending on your origin city

* These rates for partner programs are all dependent upon finding low-level award space on Delta. In other words, it’s probably not happening. So don’t transfer miles to these programs with the intention of redeeming for domestic awards on Delta unless you’ve verified space.

Hawaiian Airlines

  • 25,000 – 40,000 Virgin America Elevate points one-way
  • 40,000 Hawaiian miles one-way
  • 60,000 Korean Air SkyPass miles round-trip
  • 80,000 Virgin Atlantic FlyingClub miles round trip

The challenge with Hawaiian is that they don’t fly to Dallas, so these awards are a bit less relevant, given the need for positioning flights.

So of these options, and given CLH’s mileage balances, our first pick should probably be to try and redeem 40,000 Delta SkyMiles each way for flights on Alaska. Delta SkyMiles is a transfer partner of American Express Membership Rewards, so there would be plenty of miles for two roundtrips.

Is there award space?

For flights to Hawaii on specific dates in summer, this is going to be the real challenge. If we want to redeem SkyMiles, then all of our flights need to be on Alaska. Alaska flies between Dallas and both Portland and Seattle, so there should be some options there, but the flight to Lihue is going to be harder.

So, is there any award space in first class for two people between Seattle and Lihue that week?


No. What about from Oakland or San Jose?


Yes! The challenge with the Alaska flights out of the Bay Area though is that they are very bad for connections. They all leave at 7AM, which means our travelers would have to spend the night en route.


So let’s look at San Diego.


Plenty of space each day, and as the flight leaves a bit later that helps with the connections a bit.


However, the only way to get to San Diego on Alaska is via Portland or Seattle. That’s enough flight time that you would still have to overnight, realistically. There also isn’t any first class award space between Dallas and San Diego on either the 18th, 19th, or 20th.


We’re now looking at flying Dallas > Portland/Seattle > California [overnight] > Lihue. Those 40,000 SkyMiles for the one-way are looking like less of a deal for the one-way.

Does a lack of space change your flexibility?

Confronted with the idea of three flights (some in economy), and an overnight, many people are going to be open to being more creative. So it’s time to consider options:

  • Can they maybe leave a day earlier, say on the 17th?
  • Can they purchase some positioning flights to streamline the itinerary?
  • Does it make sense to spend a few more miles for a better routing?
  • Some combination of the above?
  • etc.

These are very individual questions, and you have to answer them for yourself each trip.

Leave early?

Based on my experience with honeymooners, leaving earlier is probably not going to be an option, though there is first class space on Delta at a reasonable-for-SkyMiles rate on the 17th:


Buy some flights?

American operates a nonstop flight between Dallas and San Diego that would arrive in time for the 10AM flight to Lihue, but it’s pricey to purchase:


Not a deal breaker, necessarily. The better option, if we can find space, is going to be looking at purchasing a flight between Honolulu and Lihue, as that should open up more routes from North America as well.

Best award options to bigger islands?

In addition to everything listed above, if we’re considering Honolulu and Maui as options, that opens up two more carriers:

United Airlines

  • 30,000 Singapore KrisFlyer miles one-way
  • 35,000 Miles & More miles one-way
  • 37,500 Avianca LifeMiles one-way
  • 40,000 Aeroplan miles one-way
  • 40,000 United miles one-way

Virgin America

  • 75,000 – 150,000 Virgin Atlantic FlyingClub miles round trip
  • 90,000 Hawaiian miles roundtrip
  • 79,000 – 137,000 Singapore KrisFlyer miles one-way

Booking United through Singapore would be a great option given the mileage balances we have to work with, so let’s start there.

Building an award for travel on United

After looking at space between all the United hubs, I found space between San Francisco and Maui:


That’s it. And there’s nothing at the saver level between Dallas and San Francisco, so we’re back to the same challenge of needing to buy positioning flights. Tickets between Dallas and SFO are comparatively reasonable, and the flight leaves late enough it would be possible to connect, but now we’re looking at buying flights to San Francisco and also to Lihue.

This still might be the best option though.

Getting frustrated yet?

I am, and this is why Hawaii is my least favorite award destination on the planet. If you want to fly economy from the West Coast it’s great, but otherwise finding award space to Hawaii can be an epic PITA.

So if it were my sister, at this point I’d probably recommend she go to Bali or Greece instead. It’s not that many more miles, and would be much more comfortable! 😉

Assuming that isn’t an option, let’s look at other alternatives.


While Hawaiian might have the most annoying frequent flyer program of any US-based airline, there are some potentially interesting values if you redeem partner miles.

The challenge there, however, is that Hawaiian subdivides their award space, and partners get a very very very limited subset. I don’t see any space to Kauai that week, and if we’re considering flights to other islands, the options on Hawaiian just aren’t as compelling.

Virgin America

While this isn’t the least expensive option, it definitely has the best availability. This is a new route, and you can redeem 75,000 Virgin Atlantic miles for round-trip first class awards between San Francisco and Hawaii.

When I called, they had space every day on this schedule:


So for 150,000 American Express points round-trip for both of them, this is potentially an interesting option. It’s certainly better than spending that many miles for Delta economy! Of course, the downside is you’re either redeeming more miles for the Dallas > San Francisco flight (which isn’t that expensive in this case), or purchasing those tickets. You also still have to organize the intra-island flights.

But there is space, every day, which counts for something.

So which option is really best?

That comes down to a conversation between CLH and the travelers, ultimately. If they have a bit of flexibility, 60,000 KrisFlyer miles each for the United flights out of San Francisco aren’t a horrible choice. If the schedule is more important, redeeming Virgin Atlantic miles on Virgin America might make more sense.


Either way, they’ll be looking at purchasing some extra flights, or redeeming separate miles for some of these tickets. It’s just not going to be practical to get this all on a single award, unfortunately.

Bottom line

Sometimes there just aren’t any good options, and this is one of those times. If CLH had American miles this would be a bit easier (in this case — not always!), but with the miles available there aren’t really any amazing choices.

Personally, I would probably look at alternative destinations (I know, other people don’t want to do that), or consider purchasing tickets outright. That’s partly why I always have a cash-back card in my portfolio, or at least something that gives me flexibility when I do need to purchase a flight.

I wish I had a magic solution, or even one that made me seem super smart, but I don’t think it’s going to happen this time, unfortunately.

Regardless though, I think spending 120,000 British Airways miles per person is a terrible value, and shouldn’t be the default choice for premium cabin awards to Hawaii.

What would you do? Anyone have any other ideas?

  1. Very thorough post, however, maybe with the exception of Virgin America, all first class product to Hawaii is borderline terrible so I wouldn’t go out of my way to book a first class ticket.

  2. Whats the deal with forum lately? Seem to go up and down all the time?
    Getting this message again.
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  3. Very well written and informative. Really insightful to see how your go through the process of tackling this itinerary. Keep up the great work!

  4. I’m trying to do my own sleuthing to help — here’s a question. Does anyone know how Delta fare codes their awards, and what a saver level award is coded as for domestic first? I’m trying to search on Delta’s website to see if saver award space exists, then leverage miles with a SkyTeam partner…

  5. @Luis: Delta does offer flat-bed service nonstop from ATL-HNL on an A333…but booking it at a reasonable award level is another issue.

  6. We go through this every year. Our daughter lives in Hawaii. We have 3 people to fly to see her. We like to switch around our islands. We always visit 2 during our visits. And sometime we base our islands on where the award seats are.

    Since we are in Texas a lot of times that means a stop over on the west coast. I have had a terrible time finding seats from Texas…economy or first class. So we will sometimes fly to west coast in coach…and then upgrade to first class from west coast over. That being said we find that there is no first class product worth it to go to and from Kauai! So now we save our miles and always go coach to Kauai.

    But we always have a hard time finding award seats to Kauai!!! Just keep checking!!

  7. @Tiffany
    Very thoughtful write up, and kind of you to empathize with our (probably infuriated) friend, CLH. I too am looking for specific dates to OGG next July, and award availability is a drag.

    I agree with @Luis about the domestic F seats, but the thought of coach for 10+ hours each way sounds like a terrible start and finish to our vacation. I guess that’s what happens when flying from DC to Hawaii. It makes the hop to Europe seem quick!

    We’re also considering using our SW Companion Pass to position to the west coast before using avios, but that would seriously make for a 12 hour travel day with at least a couple stops. If only there were saver award space on that EWR-HNL UA 767…. 120k SQ miles would be the bargain of the century…

    A guy can dream, eh?

  8. @ Dave — That’s sweet of you! Domestic first should be R, or O for the premium transcons. If you see two letters together (i.e. RL) then it’s not at the lowest level.

  9. @ No Name — I know, and it’s super super super annoying. The tech team is working on a fix, but they haven’t been able to explain to me why this is happening, so not sure when it will be working consistently again.

  10. Wow!!! That is a very well written report. Congrats!!! I took my family of 4 to Hawaii in the last 2 summers and was lucky to be able to book 3 award tickets for wife and kids on Premium Economy using Delta miles at a very reasonable redemption. I usually pay for my ticket anyway so I can get more miles so Hawaii has been a very good destination for me to put my Sky Pesos for a good use.

  11. A southwest rep recently told me they will be flying to the Hawaiian Islands in 2016. Anticipating in 1st quarter. Has anyone heard the same?

  12. Flying to Maui we’ve found tons of economy space on UA…the 5.5 hour flight isn’t bad knowing you’re headed to paradise. We even took 4 kids this past summer. And honeymooners in love might be less cognizant of the crappy UA hard (and soft) products to Hawaii. Time it right through SFO and go visit the AMEX lounge, good food and room to relax.

  13. I agree with Luis. I have flown ATL-HNL and DFW HNL many times over the past few years for work, always in economy. When I exit through the upper class section I can’t believe the mess: it looks like there was a frat party going on. Delta in Comfort+ is really not a bad option for flying to Hawaii. Just bring a meal and sit back and enjoy the free movies. The real vacation starts when you get off the plane. Save your miles for destinations where getting there is part of the adventure.

  14. @Paul
    If that’s true it would become the route with the most Companion Pass flyers ever…

    Man I hope it’s true.

  15. You’re missing one little feature of AS’s program; if you take the allowed one-way stopover (similar to using the “free international gateway” stopover AA had for years), you can effectively get an F seat to anywhere AS flies to in Hawaii as an add on to any AS partner award.

    Thus: BA LHR-SJC(stop)-LIH, KL AMS-ORD(stop)-PDX-OGG, or AA ZRH-JFK, AS-LAX-SEA(stop)-KOA (the last award is one I’ve booked).

  16. Okay, here’s how I would plan it. Transfer 85,000 MR points to Hawaiian and book coach tickets from PHX to LIH for 42,500K a piece. It might be between 5-10k more if you don’t have the Hawaiian Airlines mastercard from Barclays. Then use Avios points to get from DFW-PHX. The HA tickets would be from July 19th to July 29th. There is availability on AA in 1st class that would get you to PHX the same morning July 19th,AA flt. 1942. Then since the flight back from LIH gets into PHX at 10pm they would just overnight it and take one of many AA flights leaving PHX using again Avios points. Again you could fly 1st class from PHX to DFW. Having flown over a dozen times to Hawaii, in both 1st and econ, it’s rarely worth the extra miles to get 1st class. However, flying on HA from PHX to LIH, you can generally upgrade to snag some seats with more leg room from about $70 a piece. I hope this helps.

  17. You’re missing one little feature of AS’s program; if you take the allowed one-way stopover (similar to using the “free international gateway” stopover AA had for years), you can effectively get an F seat to anywhere AS flies to in Hawaii as an add on to any AS premium partner award.

    Thus: BA LHR-SJC(stop)-LIH, KL AMS-ORD(stop)-PDX-OGG, or AA ZRH-JFK, AS-LAX-SEA(stop)-KOA (the last award is one I’ve booked).

  18. Tiffany,
    I think what CLH made could be a very simple mistake–use BA to search, but NOT segment by segment. From my experience–I hardly (ever?) see BA website finds awards with more than ONE stop, which eliminate most of the options in this case–my guess is if he/she searches DFW-HNL it would have been a totally different story, and hopefully adding an HNL-LIH segment on HA wouldn’t be too hard either using mile or cash.

  19. @Paul, If that is the case I need to find a way to get the Companion Pass again!

    I’m currently using my SW CP for mainland and some international flights. Adding Hawaii would make it incredibly valuable.

  20. If CLH is not concerned about getting a good value, s/he could redeem for 2 F tickets on the AS flights from SAN-LIH (18th, 19th or 20th) and then LIH-SEA redeye (on 28th) using 160k Delta miles transferred from MR– and then book tickets on AA using Avios separately. On the 20th, there is availability on the nonstop DFW-SAN at 07:15, and on the 18th and 19th there is availability connecting through PHX that would arrive in SAN on time. There is plenty of availability SEA-DFW on the 29th. Not a very good use of miles though.

    I think for VX, the SFO/OGG flights on M, W, Th, F are timed in such a way that connecting to and from DAL is possible without an overnight in SFO.

  21. What’s the price for AAnytime awards on American? It might not be worth all that hassle to save a few thousand miles. I’d look into DFW-OGG or DFW-HNL with a almost never ending supply of connections on Hawaiian to Lihue.

  22. Unless I’ve misunderstood, in your AS example via San Diego there’s no reason why Dallas to San Diego needs to be on Alaskan. Availability permitting, you can fly DFW-SAN on AA (I assume they fly that route?) and then SAN-LIH on AS.

  23. In this case, would it make sense to transfer MR–>SPG–>AA?
    180,000 MR = 60,000 Starpoints = 75,000 AAdvantage miles = enough for 2 F tickets to Hawaii using a combination of AA and AS.

  24. Is access to the “ask lucky forum” only for select members?
    I get a blank screen when I try to access it.

  25. I feel the pain for booking Hawaii from DFW I thought it would be so much easier than our last home in ATL…Wrong. You can get a lie flat seat on DL but have to route through ATL to do it adding hours to the trip. So next preferable is nonstop 8 hour flights. We usually do 2 islands so open jaw with a island hopper in between is the way to go. There is a direct flight in business saver AA to OGG and HNL and I play with one way availability to from HNL, OGG, LIH ( I think there is one short route return flight from LIH) as well as flights that go through PHX that have good aircraft both legs. If non stop is unavailable, PHX is about halfway and the best routing…we used USair flights through there before leaving Hawaii late evening and waking up in PHX the next day was a good transition back to continental time zones.
    Unfortunately availability has only gone down during merger mania ( I haven’t checked lately), but unless your able to plan one year in advance, or jump on tickets available 3-5 weeks out, finding 2 really good seats is a frustrating endeavor.

  26. @ eponymous coward — Indeed, and have done that myself. The problem is our friend doesn’t have Alaska miles in this case.

  27. @ Jeremy — If they had AA miles, that might not be a bad option. But I think buying a ticket (if reasonable) is probably going to be a better value.

  28. @ Callum — Because they would be using Delta miles for the Alaska flights they wouldn’t be able to include the American flights on a single award.

  29. @ gj — No, it should be open to everyone. Not sure why that’s happening, but thanks for the heads up!

  30. Hi there – thank you to Tiffany for this wonderfully comprehensive post, and to everyone for chiming in with suggestions. I have gone through and checked each one but unfortunately I believe Tiffany is right that paying for a ticket is going to be a better value. I cannot find anyway to use my MR rewards (200k) or Avios (200k) to end up with 2 first class tickets from DFW-LIH.

    Because their hearts are set on Hawaii, choosing Bali or Greece will not work (though I’d personally agree to change the destination too!). So I think the best I can do is to offer them the Virgin America flights from SFO-OGG or HNL in first class. Or economy all the way on Delta for miles and pay cash to upgrade them to Comfort plus. I realize that is not a good use of miles but paying cash for the 2 economy tickets would cost around $2500-$3000, so using the 160-180k MR points to save them the money is worth it to me. Now that I am following this blog and using the credit card strategies, I think I’ll earn back the points and miles soon enough.

    I have definitely learned a lot through this exercise, and I am hoping that following examples here will help me spend those BA miles in a useful way eventually.

    Thanks everyone!

    P.S. I am having similar problems accessing the forum – I keep getting the same message: “An unexpected database error occurred. Please try again later.”

  31. @Tiffany Oh yeah, so they are.

    I hope you don’t take this as a criticism as it’s a brilliant post, as everyone else is saying, but it seems a bit needlessly complex and confusing! You could cut out a huge amount of the descriptions, keeping the important information and making it a lot easier to follow.

    Though I do realise you were posting your thought process for their particular scenario and not a general guide.

  32. We got 4 first class flights from NYC-LIH for January on US Airways/AA with AA miles via Phoenix, and 3 on the way home on AA via LAX (have kids under 2 – man it’s gonna be a long flight for us). Not the best first class, but better than coach for such a long flight, plus we got 10K of the AA miles back since we have the credit card.

  33. I posted this on the Ask Lucky forum, but just wanted to put it here too, in case anyone else is trying to book tickets to Hawaii. There is a happy ending to this frustration!

    Woohoo! I did it – I booked 2 first class tickets to Hawaii. Not on Virgin – I called Virgin Atlantic and they told me they could not book Virgin America tickets to Maui because the route hasn’t started yet and therefore isn’t in their system (even though tickets already for sale on Virgin America site). The rep was really kind and tried to help me find a way to book the tickets using Virgin miles, but there was no way to make it happen without a really awkward connection, an extra night in SFO and still paying for intra-island flights.

    But, I found a few extra Delta Skymiles hiding in my account (which doesn’t show up in Award Wallet so I didn’t realize they were there). And my last round of MR points posted, plus the lovebirds were able to shift their dates by 1 day to fly on Sunday 17th, so I was able to buy two tickets at 110k each, total 220k Skymiles for the two tickets which are DFW-LAX-LIH. Only one connection is pretty nice and not having to purchase extra flights is worth it.

    I realize it’s probably not the best value anyone ever achieved with MR points, but my sister and her fiancé are thrilled, and I’m so happy I could give this to them.

    Thanks again for all of the tips and suggestions and encouragement. Now I think I’m off to apply for a Citi Thank You card, since I clearly need to earn some more points.

    P.S. Special BIG thanks again to Tiffany for writing such a great comprehensive post which is really helpful on understanding award bookings in general!

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