Reader’s Request: Help Me Maximize My Existing Stash of Miles and Points for a Family Trip to Hawaii

First, let me address the elephant in the room. Namely, that this topic has been covered ad nauseam in the miles and points blogs. Still, I think it’s helpful to see a practical application now and again.

Out of all the emails I get from readers, I would say at least a third has to do with trying to redeem miles and points for a trip to Hawaii. It’s a Holy Grail of destinations when it comes to family travel. And for a good reason: Hawaii state is exotic, scenic, diverse and relatively affordable for a tropical destination. It’s even sometimes called a “poor man’s Tahiti.” Yet, it’s part of the US, so no passport is required and English is the main language, though spoken with a Hawaiian flair.


Enjoying the scenery in Kauai 10 years ago, BC (before children). The white dots you see in the distance are actually birds.

I’ve been to Hawaii twice and highly recommend it. My goal is to take the kids to Kauai one of these days but for now, I’m going to live vicariously through helping others make this trip a reality. Be aware, this is a “mother of all posts” write-up, meaning it’s long and detailed. Without further ado, here is the gist of the email, followed by my advice:

“We are a family of four, and one of our kids will be turning two later this year. I’m hoping to visit Hawaii before that happens, so we can bring him for free. That means we will  need three award tickets. I would also like to cover hotels and a rental car with points,  in order to reduce out-of-pocket expenses as much as possible.

We have:

1) 150K Ultimate Rewards points

2) 110K Membership Rewards points

3) 60K Thank You points

4) 200K AAdvantage miles

5) 80K United miles

6) 30K Delta miles

The strategy for flights

I always say that before worrying about hotels, you need to secure your award tickets first. I’m not sure where this reader lives, so I’m going to give general advice on best mileage bargains out there. Normally, the suggestions will depend on your geographic location because some programs are distance-based.

I assume that you have one of premium cards with Chase (Chase Sapphire Preferred or Chase Ink Plus) and Citi (Citi Thank You Premier or Citi Prestige). Those enable you to perform transfer to miles and hotel points programs.

1) Korean SkyPass program

The miles transfer instantly from Chase Ultimate Rewards 1:1. This is hands-down the cheapest option for vast majority of US population. However, there is a catch, several, in fact. You have to find low-level award tickets on Delta, Korean partner. You also have to book roundtrip tickets because one-way partner awards are not allowed.

The cost in economy is only 25K miles roundtrip, and in business/first class it’s a ridiculous bargain  at only 45K miles roundtrip. By comparison, Delta charges 45K miles roundtrip in economy and 80K miles in business (or more) for the same exact flights. This reader has enough UR points for three seats in either class.

If you can find low availability in business/first on Delta, absolutely consider splurging, especially if you are flying from the East coast. So, what you have to do is search availability  on Alaska Air website because it will display low availability on Delta as well. Then you contact Korean Sky Pass program to see if the seats are available.

It’s a tedious process but apparently, not as bad as I thought. The best part is that you can put your award seats on hold before transferring Ultimate Rewards points. That’s huge, huuuuge! Read this post on The Points Guy on how one writer was able to secure four seats in first class on Delta using Korean program. It outlines all the steps. #Impressed

2) British Airways Avios program 

The miles transfer instantly from Chase Ultimate Rewards 1:1 and Membership Rewards 1,000:800. I would stick to UR currency and save MR points for another award where I could transfer them 1:1. Avios is a distance-based program that would mostly be of use to those who live on the West coast, specifically large cities like Los Angeles, Seattle, Portland, San Diego and a few others.

The cost is 12,500 Avios miles one-way for nonstop routes, and the flights would be on American Airlines or Alaska Air. Check this post on MileValue that will show you all of your available options. You can’t book Alaska Air flights on, but American flights usually do show up. Search and if you find “low” availability pricing at 22,500 miles, cal Avios center to reserve your award tickets (ask for fee waiver).

Important! Before I make a flexible points transfer to a partner airline program, I always call and confirm award availability. Just because is showing an award flight, doesn’t mean it will be available via Avios. Something else to keep in mind is that very often Avios will not show AA award flights with connection. You will need to call Avios center and the agent should be able to help (once again, ask them to waive the fee).

It’s not really an issue for non-stop flights from West coast to Hawaii, but just something to be aware of. Side note: check my post on Avios program and why it’s a winner for many American families.

3) Singapore KrisFlyer program

The points transfer 1:1 from Ultimate Rewards, Membership Rewards and Citi Thank You program. This will probably be your best option since United Airlines (a partner) seems to have the best availability to Hawaii.

It costs 17,500 miles one-way to fly from Mainland to Hawaii in economy and 30,000 miles in business class. You won’t be able to search availability on, but would need to do it via United website. Once again, the pricing  will be  different, just ignore it. What you are looking for is this:

boston-maui united

The flights need to be on United metal (UA letters), and economy  award should price out at 22.5K via United, and business class at  40K miles one-way.

If you can find availability, call Singapore airlines office in USA and try to get them to book the flights using KrisFlyer miles. Be aware, I saw various reports on Flyertalk saying that Singapore agents tried to add extra $100 tax to the award ticket. That’s incorrect since United does not impose fuel surcharges on award tickets. If you experience this, you need to HUCA (hang up call again) and insist on correct tax of $5.60 one-way.

Unfortunately, the transfer from Citi Thank You, UR and MR programs takes 1-2 days to go through, so I recommend you have a Plan B ready, just in case. Your desired United flights might be gone by then, especially if you are looking to fly during a popular time of the year. Some have been able to put award tickets on hold without having any miles in their account, so check with Singapore agent and beg them to do it.

One important note: If you happen to have Chase United co-branded credit card, you will probably see more award availability when logged in. You should log out and perform a search again. That’s because United provides extra award availability to those who have their co-branded card. Obviously, Singapore program can not give the same perk, so they will only see award flights available to general public.

4) Air France Flying Blue program

The miles transfer instantly 1:1 from Ultimate Rewards, Membership Rewards and Citi Thank You program (last one takes a few days). I did  analysis of this option for flights to Hawaii last year, and here are my findings:

I have to say, this is one quirky program. I don’t know what their logic for pricing awards is, but as my post has pointed out, Kauai-Boston route was running at only 12,500 miles one-way.  Officially, it should be 15,000 miles. Also, unlike other foreign programs, Air France has several tiers for redemption on partners. What that means is that even if Delta doesn’t have any saver (lowest level) award seats,  you will still be able to book them via Air France (a partner), albeit at a higher price.

air france kauai-boston cheap

Notice how some dates return pricing of 25,000 miles one-way? That pattern appears to mimic Delta variable pricing on its own website, although, the rates are a bit different. This is actually to consumer’s advantage because it gives you more options.

Let’s say you redeem 25,000 miles one-way instead of 12,500 or 15,000 (will the real rate stand up?). It can still be a good deal compared to what revenue flights run on most routes from the East coast. Business class redemption starts at 37.5K miles one-way, and the same principles apply.

Naturally, you would want to utilize the lowest possible award level and leverage flexibility to your advantage. In order to get the most accurate picture, you probably would want to start on and do a  search there:

delta, no codeshare

If you are looking for an economy flight, you want to make sure of two things: 1) The award prices at 22.5K mies one-way on Delta website, 2) There are no codeshares, so you only see DL letters at the top. That’s because Air France will not be able  to help you with flights operated by Delta partners. See this post for more.

OK, so, you found the flights and everything is in order. Now, march on to Air France website and perform a search there. The award should show up, if not, you may need to call and give Flying Blue rep specific details so he/she can look it up manually. Read this post for more information on transfer to Flying Blue from Citi Thank You program.

5) AAdvantage program

While this is a more expensive option than the others I’ve listed, it’s worth considering. Why? In case you want to save your flexible points for hotel/car rental or just another airline transfer. If you don’t have any specific plans for AA miles and want to liquidate them, it may be worth it to use them on this route, especially if you live on the East coast.

Here are the prices:

aa hawaii

It’s 20,000 miles one way during off-peak, 22,500 during peak season.

MileSAAver Off Peak Dates:

This reader has 200K AAdvantage miles, plenty for three roundtrip tickets in economy. In fact, he could even book  business class one-way at a  cost of 40K miles per person. Obviously, this is not the cheapest route compared to the other ones I’ve mentioned, but it’s an option.

If you live near AA hub on the East coast and find decent flights on American and/or Alaska Air, consider burning your existing stash.  Be aware, if the routing includes inter-island flights on Hawaiian Airlines (AAdvantage partner), you will pay extra miles for those connecting flights.

Fortunately, since you are not using a partner program to book awards, all the prices will be clearly displayed via online search. You can put AAdvantage awards on hold for up to five days at no cost while you explore other options.

The same principle applies to United program. Notice how this reader has 80K miles? If he wants to liquidate them, it could be worth it to transfer 10K UR points in order to book two roundtrip tickets. Then use Citi Thank You points for transfer to Singapore in order to get the third award seat at 35,000 miles. Of course, first, you’ll need to make sure that there are three low-level (45,000 miles roundtrip) tickets available on

All things being equal (or close to equal), try to always burn your miles and save flexible points if at all possible. 

6) Hawaiian program (when there is a bonus on transfers) 

Hawaiian miles transfer from Membership Rewards 1:1. I’ve mentioned last Friday that there is a 25% bonus on transfers running through 6/21/2016.  The best deal is non-stop route from New York to Honolulu.

Regular price in economy (saver level) is 20,000 miles, so you would need to transfer 16,000 MR points in order to cover one-way ticket, which is pretty good. Of course, first, you need to find award availability. For most people, the best use is to redeem the miles for inter-island Hawaii flights (regular price is 7,500 miles one-way), where availability is usually excellent. See more information  on this program as well as routes here

7) Virgin America program (when there is a bonus on transfers) 

There isn’t one going on right now, but it’s worth keeping an eye on this option. Normal transfer rate is 2:1 form Membership Rewards as well as Citi Thank You. Virgin America has a revenue-based program, meaning you don’t have to worry about seat availability. You get 2.2 cents per point.

They have non-stop flights to Hawaii from Los Angeles and San Francisco, and you can even use points to book a connecting  flight from other airports as far away as Newark. It’s very easy to see the cost in points and you can do it by checking various routes on this page You don’t have to be a member in order to perform the search.

I wrote a post on Virgin America and its partnership with SPG (where points transfer 1:1), and recommend you read it to see various sweet spots. Virgin America also partners with Hawaiian airlines, so this could be another way to leverage the points.

The strategy for hotels

Don’t limit yourself to hotel points! There is more than one way to skin a cat. Depending on which currency you used for award tickets, you have several options:

1) Transfer Ultimate Rewards points to Hyatt program 1:1. There are several nice Hyatt properties in Hawaii, and most cost 25K points per night. To me it’s a bit expensive, but to each his own. Check my post on various award hotel options in Hawaii.

2) Use Ultimate Rewards points to book a non-chain hotel and get 1.25 cents per point. I recommend you always do a search via UR travel portal and see what comes up. There may be a perfectly lovely hotel that costs 15,000 UR points per night and includes breakfast.

3) Cash out UR points at 1 cent a piece and use the money to book a rental on VRBO or similar site. Yes, I said it! I also strongly recommend you look into booking a hotel through Unlike, you can put in four people in your search.

My cousin-in-law was able to get this nice beachfront resort in Kauai through Hotwire for a $125 per night. She said she liked it almost as much as Hyatt. If you cash in 25,000 UR points and get $250, you’ll be able to get two nights at this hotel compared to just one if you chose to transfer points to Hyatt program instead. I know it’s “apples to oranges” kind of thing, but something to think about. Before booking a hotel on Hotwire, do your research on Betterbidding website.

4) Use Thank You points to book a non-chain hotel, similar to what you would do with UR points. If you have a Citi Thank You Premier card, you’ll get 1.25 cents per point. Otherwise, you’ll get 1 cent.

My reader Audrey has also reminded me of “4th night free” hotel benefit that comes wth Citi Prestige. You do have to pay revenue rate for the first three nights, and Citi will comp the last one.

5) Redeem Membership Rewards points on AirBnB gift cards and get $1,000 in value per 100K points. I wrote about that option in this post

6) Use AAdvantage miles if you happen to have a co-branded AA credit card. I wrote about this option before and actually cashed out my AA miles at a penny each in order to book a rental in Key Largo. The same principle applies to Hawaii. I did a random search at the beginning of August, and here is what came up for Maui:

hawaii on AA miles

These are all beachfront resorts, and you get a studio or 1-bedroom unit, not just a tiny hotel room.

Car rental options

Once again, there are a few options:

1) Use UR points and get 1.25 cents towards car rental cost. If you happen to have Chase Sapphire Preferred, make sure to pay part of the cost with it because it provides primary insurance coverage.

2) Use Citi Thank You points. If you have Citi Thank You Premier, you’ll get 1.25 cents per point in value, otherwise, 1 cent.

Both Chase an Citi portals usually have the best prices on car rentals, but always check other options just in case.

What I would do if it were my trip

One can only dream! For flights, I would absolutely try to book business class seats via Korean Sky Pass program. Shocked? Flying to Hawaii from Florida is similar to going to  Europe, distance-wise. And paying 45K Ultimate Rewards points for a nice comfortable seat is a steal. This is an amazing deal, and may not be around much longer. As much as I love UR points, I would dump them in a heartbeat for this sweet redemption.

However, like most families, we are limited by school schedule and it would be unlikely to find saver business class on Delta for four people on this particular route. So, I would check and see what other award flights were available. Then I would pick the winner based on the least amount of potential misery (as in fewer connections, shortest layovers, better departure times etc.)

Those factors are very important to me since we have small kids. I would try to redeem miles on business class if at all possible, but I wouldn’t do it if it meant adding extra connections and longer routing.

In all likelihood, United would be the best option,  so I would transfer Citi Thank You points and Membership Rewards to Singapore KrisFlyer in order to have enough for four tickets. United miles are valuable to me, so I would save them for another redemption.

It does depend, though, on whether I was planning on canceling a premium card with Citi or Amex in a near future. If I needed to find some decent use for MR points ASAP, I would dump them first and then dip into Citi or Chase stash. So, YMMV

As far as hotels go, I would take a look at VRBO and other vacation rental options and if nothing appealed to me, I would burn AA miles on a 1-bedroom oceanview unit. I’m just not that into Hyatt, although my current Diamond status could possibly sway me  if I was able to get a suite upgrade and free breakfast.

Side note: if you are visiting Hawaii for the first time, my advice is to split your stay between Maui and Kauai. However, I strongly recommend you  do your own research because it’s impossible to say what will appeal to any specific individual. I thought for sure my father-in-law would love Kauai, yet he didn’t. His and most travelers’ favorite Hawaiian island is Maui.


Watching a beachfront luau in Lahaina.

Either way,  when it comes to visiting Hawaii, no matter which island you pick, you can’t go wrong. Personally, I’m partial to Kauai, and here is why:


Readers, what do you think of my analysis? Anything you would like to add?

P.S. If you are just starting out in the hobby, check out my Free Consulting Service I’ll be happy to put together a specific plan on how you can visit Hawaii or any other destination with minimum out-of-pocket costs involved.

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11 thoughts on “Reader’s Request: Help Me Maximize My Existing Stash of Miles and Points for a Family Trip to Hawaii

  1. I never get tired of reading about Hawaii! My husband gave me the green light to plan a trip for early 2018. I’m thinking of a split trip between Maui and Oahu. I need to see how many airline points we have left after getting to Vancouver to see how we can fill in the gaps to get the flights we need. This post is a great resource.


    • Nancy, what??! Another trip to Hawaii? 🙂 I’m jealous. I really think you’ll enjoy Maui, especially if you go during whale watching season. Winter and spring would be the best time to spot humpbacks. In Maui oceanfront condo or hotel is the way to go, I think. You can watch whales play in the water right from your balcony. I did enjoy Maui a lot, but Kauai is my favorite Hawaiian island so far.


  2. Forgive me if this was covered and I missed it:
    1) 4th night free on Thank You points if you have Citi Prestige
    2) Avios are per segment, so more if flights are connecting, no?


    • @Audrey Great feedback, as always! I did imply that Avios fights have to be non-stop, but perhaps didn’t make it super clear. It is mentioned in the both posts I’ve linked to.
      Good point on Prestige. To be honest, I forgot about the benefit, and my overview has to do with reducing out-of-pocket costs. You have to pay cash for three nights in order to get 4th one free. But it’s definitely a nice perk, and I will update the post.


      • When you said “Avios will not show American award flights with connection” so you have to call, I took that to mean it was desirable, as I said maybe I missed your point.
        As for Prestige, I’ve actually never used this benefit and actually didn’t know you don’t use Thank You points to pay fourth night free (brand new to the program). Certainly good to know!


    • @Audrey No worries! I want to make my information as clear as possible, and reader’s feedback helps me to achieve that. I did go back and changed the verbiage to “non-stop rote.”
      As for Citi hotel benefit, I’ve never used it, but it’s definitely legit. Check out this post I think you can now check hotel prices online, but I couldn’t find the web address.


  3. Pingback: Leveraging New SPG/Virgin America Partnership for High-Value Flight Redemption from Portland to Hawaii | Miles For Family

  4. We have taken our family to Hawaii a few times, in fact we just booked 5 award flights from PDX to OGG for this winter. I wanted to drop a bit of a plug though. In my experience, especially if you travel off season the absolute best price for a rental car is bidding on priceline. In our 5 trips to Hawaii the most we have paid for a rental car was $16 per day for a full size car. And every time we pick up our rental car we have been upgraded in the lot to an SUV. I don’t count on the upgrade but it has been pretty consistent. I wrote about my bidding strategy on a blog of mine. Those interested in family travel should read it. It really does help lower costs.


    • @Scott Thanks for stopping by! Feel free to drop a plug anytime. I really don’t mind, especially if it will benefit my readers. I’ve never booked cars through Priceline, but it definitely looks like the way to go for Hawaii. I’ll link to your post tomorrow as well.


  5. Pingback: Should You Take Advantage of 35% Bonus on Transfers to Avios Program? | Miles For Family

  6. Pingback: A Request from Reader: Help Me Get to Maui from LAX with My Existing Stash of Miles | Miles For Family

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