Hawaii on Points – The Easy Way

My family has now taken 5 trips to Hawaii over the last few years using this exact method. If there’s one place we love using our points, it’s Hawaii! Hawaii is crazy expensive and this method saves us a ton!

Flights to Hawaii

When flying to Hawaii generally costs $700+ per person, in economy… that’s when I know 100% we will be using points for those flights. There are many different methods to fly your family to Hawaii on points.

Almost every time we fly to Hawaii, we use Southwest points & a Southwest companion pass.
If you aren’t familiar with the Southwest Companion Pass – it’s when your companion flies for just the cost of taxes when you fly… so just $5.60 each way to Hawaii!

The easiest way to earn Southwest points is via a Southwest credit card sign up offer.

Personal Card Options:

Business Card Options:

And if you want to learn more about the Southwest Companion Pass in general, I’ve got you covered.

The best way to find the cheapest Southwest flight to Hawaii is to use the Southwest low fare calendar.
This can only be viewed on desktop (not on the app). You’ll go to do a flight search, select “Points”, and select “Low Fare Calendar”…

We use points for 2 tickets and then our 3rd ticket costs 0 points due to our Companion Pass. We try to find fares that are less than 40K points roundtrip per person. Meaning, for the 3 of us, we’d need 80K points roundtrip.

When you use points/Companion Pass, you’ll ONLY pay taxes which are $5.60 each way. So for the 3 of us, it costs $33.60 for 3 roundtrip tickets to Hawaii!

I’ve also written an entire post about using other types of points/miles for Hawaii specifically. This is worth checking out to see if these options would be better for you. For example… sometimes you can find flights to Hawaii for as low as 10K miles per person each way when using Capital One miles to book on Turkish Airlines BUT fly on United. Sound confusing? It’s all explained in that link 🙂

Hawaii Hotels on Points

The easiest option, the one my family continues to use in Hawaii…
Earn Chase Ultimate Reward Points & transfer those Chase points to Hyatt for $0 stays.

We’ve done this at the Grand Hyatt Kauai, Hyatt Regency Maui and the Andaz Maui. Those hotels can often cost over $800+ night. With Hyatt award night stays, you don’t even pay resort fees… so we are truly talking $0 hotel night stay!

One of the easiest ways to find the least expensive Hyatt night stays is using a free tool called MaxMyPoint. You can search by month and see what dates have availability and how many points each night costs. After you find the date you want – go to the Hyatt site and verify availability.

We recently stayed at the Andaz Maui over spring break. At the time, the nightly rate was basically insane… $1000+ PER night!! I overheard people saying they were there on points from their Hyatt card. Smart! Because who can pay that rates?!!

But…
Since we are friends, it’s important I tell you… putting all of your spend on your Hyatt card OR staying tons of nights at a Hyatt is NOT how we earn points for these free Hyatt stays.

The quickest/easiest way…
Earn Chase Ultimate Reward Points and TRANSFER those points to Hyatt once you are ready to book.

I’ve written about this a lot and you can find more details here.

One thing I love about this method is you can earn points on many different Chase cards and then “combine” those points to 1 card and transfer those points to Hyatt. I prefer this method because I want to earn as many points as possible on each purchase.

For example….

Chase Sapphire Preferred® Card – I use this card to get 3x for online grocery & 3x on dining – these are 2 of our biggest budget items monthly so I want to maximize my point earning.


Chase Ink Business Cash® Credit Card – One of my fav features of this card is it earns 5x at Office Supply Stores (up to $25K annually).
*THIS card on its own doesn’t have “transfer” capabilities. But if you have the Sapphire Preferred card, you can combine these points to your Sapphire and then transfer them out from there.

If you aren’t sure on how to transfer Chase points, there’s a step by step resource here.

Rinse & Repeat

I use this Southwest/Chase to Hyatt strategy for almost all of our domestic travel.
Once you’ve done it once, you’ll see how easy it is to repeat. With this method we get huge savings from our points!

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