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Helping my Cousin-in-law Plan her Next Trip to Hawaii Via Miles and Points

On Friday I’ve mentioned that my cousin-in-law just visited Maui with her husband for their wedding anniversary. They came back and started planning a  trip to… Hawaii!

If that’s not an endorsement for this amazing US destination, I don’t know what is. She said that they both decided they want to bring the kids next time. So, she has reached out asking for advice on how to pull off this trip.

Her miles and points stash

100k AAdvantage miles (soon she will have 163k miles since she just got approved for Citi AA card)

145k transferrable Ultimate Rewards  points

Her preferences

She is hoping to visit Big Island and possibly Maui, but she is pretty flexible. They do hope to go during Spring Break of 2019, but next summer will work too.

Their kids are in elementary school, and they don’t want to take them out unless there is no other option. My cousin-in-law has mentioned that she would like to stop in San Francisco on the way back and maybe spend a day or two touring the city.

She is also hoping to get re-matched to Hyatt Explorist status in a few weeks. If that works out, she would definitely like to use Club Lounge certificate in Hyatt Regency Maui Resort and Spa  

If they stay in this resort with kids for 5 days, she will have to transfer 100k UR points to Hyatt program (20k Hyatt points per night). If MLife match proves to be successful, her Hyatt Explorist status will expire at the end of February in 2019, so they will have to take the kids out of school if they go this route.

She is hoping to burn her AA currency on flights, but is open to suggestions on what other cards they may want to consider in order to get the best deal via miles. Since they will be bringing kids, she wants to make the journey as easy as possible, especially since they will be sticking to coach.

My advice

Technically, my cousin-in-law has enough AA miles for four roundtrip tickets if at least one of their flights falls into off-peak period. The cost is 20,000 miles, plus, you get a  rebate of 10% via co-branded AA credit card.


That’s the good news. The bad news is that they will have almost no wiggle room on dates. As you can see, summer is pretty much blacked out, and finding four sAAver tickets to Hawaii around holidays or spring months can be very difficult.

My cousin-in-law has been fortunate so far because they were able to find sAAver availability twice. However, both times they visited during January when kids are in school. They also needed only two award tickets.

They may get lucky and find what they need, but I wouldn’t count on it. I think having a Plan B is prudent. So, here is what I think she should do:

1) Wait and see if she can get another Explorist match via MLife. Right now she is working on minimum spending for Citi AA card anyway, and is not able to sign up for any new offers. If she gets 4 Club Lounge certs, they will have to plan their visit in January or February of 2019. That means she will be able to look for award tickets with AA miles right away since you can book 11 months ahead.

2) Let’s say she can’t find any sAAver award availability via AAdvantage. Once she is done with AA card, she should consider applying for 50k Amex Premier Rewards Gold offer via Chrome or Incognito mode. I recently wrote about doing this myself. 

I told her she can come to our house and use my computer to apply. She checked CardMatch tool, but wasn’t able to see 50k offer there. Ditto for pulling it up in Chrome. Just to avoid any doubt: We do NOT make any commission unless readers use our affiliate links to apply for cards. 

Flexible points are best because they give you access to multiple airline programs. If she wants to stop in San Francisco on the way back, her best bet is to go through Singapore KrisFlyer. Singapore program partners with United, and San Francisco is their major hub.

The cost is 17,500 KrisFlyer miles, and a stopover on a one-way award ticket costs an additional $100 (it’s free when you redeem miles on a roundtrip flight). Still, even with an additional fee, it makes sense to go this route because flights from Orlando to San Francisco usually cost more than $100.

Keep in mind, you would have to find award tickets that cost 22,500 miles one-way on Those are the only kind bookable via Singapore. If you happen to have a co-branded United card, you will have to log out first because it gives you access to additional award space. Singapore KrisFlyer reps will not be able to see it on their end.

Both Membership Rewards and Ultimate Rewards points transfer to Singapore program on 1:1 basis. Technically, she has enough in UR program to cover four roundtrip tickets, which would avoid $100/per person SFO stopover fee. Unfortunately, the transfer is not instant (takes 12-24 hours), which is a serious drawback.

KrisFlyer miles expire 3 years after you earn them, which would make me a bit nervous, especially when planning a trip to a popular destination like Hawaii. So there is definitely some risk in going this route. Update: reader Micah mentioned in the comments that it should be possible to put KrisFlyer award on hold before transferring in the miles. I’ve seen mixed reports on this one, but it’s definitely worth a shot. 

3) If she is not comfortable with taking a chance on Singapore transfer and risking losing award tickets, there are several more options for including San Francisco as a stopover.

She can use AA miles to book Maui-San Francisco flights that are operated by Alaska Air, which cost 22,500 miles one way. Availability is not great during peak travel periods, but easier to spot during early fall.

As you can see, you also have an option to fly to San Jose or Oakland.

A much cheaper alternative is to go through British Airways Avios program instead. Those same exact flights cost 12,500 miles one-way. Both Membership Rewards and Ultimate Rewards transfer to Avios instantly on 1:1 basis.

Make sure to call BA center first and verify that the flights are available (they should be). Also, ask the agent to waive the phone fee because Alaska Air award tickets are not bookable online. You can then transfer MR or UR points while you have the agent on the line. Voila!

Personally, I would use Avios instead of AA miles. Not only is the price  a whole lot cheaper, but cancellation fees are much lower, too. If your plans change and you need to cancel  flights, you will only lose $6 tax/per person that you paid on your Avios award ticket. With AAdvantage you will have to cough up $150 for first person on the reservation and $25 for each additional passenger.

But what about flights from San Francisco to Orlando? You can transfer UR points to Southwest Rapid Rewards and book a non-stop flight to MCO  from San Jose or Oakland. I just booked one myself for less than 10k Rapid Rewards per person.

So, if all goes well, you can book both flights for around 90k Ultimate Rewards, assuming you need four tickets. If you happen to have Membership Rewards points, I would use those for Avios transfer.

4) The absolute cheapest way to get to Hawaii from Florida is via Korean Air SkyPass program. The cost is 25,000 miles roundtrip, and the flights are operated by Delta. It is a quirky program that could be a fabulous deal, especially for tickets in first class. You can read my post where one of my readers has shared her experience with SkyPass.

My cousin-in-law would have to set up a family account ahead of time and transfer 100,000 Ultimate Rewards points for four tickets in economy (if there is low-level availability on Delta). Unfortunately, Delta doesn’t offer non-stop flights from Hawaii to SFO. They could overnight in Los Angeles or Seattle, but she is not super interested in either option.

Their best bet for flying between the Hawaiian  islands is to redeem United currency (7,000 miles one-way transferred 1:1 from Ultimate Rewards). Another option is Hawaiian miles, a program that partners with Membership Rewards.

You may  want to read my post from few years ago: Reader Request: Help Me Maximize My Existing Stash of Miles and Points for a Family Trip to Hawaii

But what about saving UR points for Hyatt transfer?

Both my cousin-in-law and her husband are eligible for sign-up bonus on Chase Hyatt Visa. So, there is an option to apply for it down the road. I always recommend you take care of your flights first before worrying about hotels. Personally, I would not plan my visit to Hawaii based on Hyatt Club Lounge access.

Don’t get me wrong, saving money on food is always welcome when you are a middle-class family. Plus, they really loved that Hyatt resort in Maui. However, I would much rather get the preferred travel dates rather than free food and fancy pools. But that’s just me.

Keep in mind, you can always burn AAdvantage miles on  condos at a penny each if you have a co-branded AA credit card. Just buy groceries and cook your own food. Boom.

Sure, it may not be the best return on your AA miles, but with poor sAAver availability, it’s certainly worth considering if you are a family on a budget.

All in all, when it comes to miles and points, there is usually more than one way to skin a cat, so to speak. And no, I don’t actually skin cats!

Readers, what would you add to my advice? 

Click here to view various credit cards and available sign-up bonuses

Author: Leana

Leana is the owner and founder of Miles For Family. She enjoys beach vacations and visiting her family in Europe. Originally from Belarus, Leana resides in central Florida with her husband and two children.

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12 thoughts on “Helping my Cousin-in-law Plan her Next Trip to Hawaii Via Miles and Points

  1. Thanks for all the tips. I forgot about the fact that even if I was able to get Explorist again, I wouldn’t have it for Spring Break. The free food was huge deal for us and saved a ton. I also have Hilton points, so that’s an option on some of the islands. I wonder if those $350 tickets will still be around next year. That may be something to consider. I’ll just have to see what will work.

    • No worries! Yeah, the expiration timing of Explorist status is a bummer when you are planning a spring break vacation. I can understand why you liked getting that lounge access. I would, too! Food at Hawaii resorts is expensive from what I’ve heard.
      As far as getting cheap fares, definitely keep an eye on and similar sites. You may snag cheap tickets that will work for your dates. But personally, I would not count on it. If you find a good mileage redemption, I would snag it. One possibility is buying a travel insurance policy that lets you cancel for any reason. That way if you find cheap tickets later on, there is an option to cancel award flights and not get hit quite so hard with cancellation penalties. Alternatively, you can stick to combination of Avios and Southwest tickets. Those are cheap/free to cancel. Of course, then you will be stuck with Avios and Rapid Rewards Points rather than UR currency.

      • I actually found four saver tickets over winter break! Couldn’t believe it. Of course, I don’t have all my points yet. And then my husband informed me we probably can’t go over winter again. That’s peak time at his employment, and apparently things kind of fell apart last time while he was gone. (Good to know he’s not expendable!) So we are down to Spring Break without lounge, summer if we could find award seats or taking kids out of school for a week. We have some options. I do need to heed your advice and get more flexible points though!

        What are the data points on canceling Hyatt cards and getting approved again? I sure hate to take a chance on losing my anniversary certs.

    • I can’t tell you the exact timeline on canceling and reapplying for Hyatt card. I would think waiting a month would suffice. What you may want to do is cancel yours first and have your husband refer you, so he can get bonus 10k points.
      I can’t tell you what to do because the card may very well be subject to 5/24 when you get ready to apply. But so far, it hasn’t been affected. I would be tempted to try. Sure, you may lose your anniversary cert. On the other hand, you may get 55k points factoring in referral bonus.

  2. I would use UR points to transfer for flights, and personally with kids, I love having a condo (kitchen & laundry). We have stayed at the Hyatt resorts on Maui and Kauai, and the pools are so much fun. However, we only stayed for 2 and 3 days at each one, and I think if we stayed any longer, mommy would have gone a little kookoo since there’s not much space in the rooms. We’ve been to Hawaii 3 times, and it’s one of my favorite places to visit especially with the kids.

    • @Stephanie If I lived in LA, I would be tempted to fly to Hawaii a few times per year! I agree with you on condos. I can only tolerate a maximum of three nights with kids while sharing one room. That’s it. No fancy pool can make up for mommy going kookoo for Cocoa Puffs. 🙂

  3. We’re doing Kauai and Maui in April of this year. Grand Hyatt Kauai and Fairmont on Maui. Sounds like you may need to do a round table discussion of all of our experiences and thoughts!

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