Saving Money Tips

Flying to Hawaii on Points!

We flew our family of 6 from Salt Lake City to Maui on Delta last year with some of our points/miles and only $56.00 total ($5.60 each way)! Then my husband and I went on a romantic trip to the Big Island flying from SLC to Kona on Delta for only $22.40 (also just $5.60 per person, each way!).

This year we flew to Hawaii on points AGAIN as a family of six from Salt Lake City to The Big Island round trip on points as well via Southwest for only $67.20 TOTAL (so 33.60 total each way)! Here is a breakdown of the cards we used, how we earned our points, how we booked, and how you can do it too! 

Flying to Hawaii on Points

Hawaii is a dream destination for many families but the steep cost of airfare from the mainland can be a deterrent. One of the best ways to bring down the cost of a family vacation to Hawaii is to reward travel and book your flights on points and miles! 

If you are new to the world of reward travel you can read all about the basics as well as the pros and cons here – Reward Travel 101

You can also get our free Points & Miles Crash Course here!

flying to hawaii on skymiles
Traveling with my little loves is my favorite thing to do and it wouldn’t be possible without my points and miles!

The Cards We Used to Help Us Earn Points for Hawaii ON DELTA

Last year knew that we wanted to fly Delta to Hawaii. (My husband flies Delta a lot for work and we get amazing loyalty perks. So we try to fly with Delta whenever we can.) Because Delta is a partner with Amex, we knew that we needed to earn Amex points and then do a direct 1:1 transfer to Delta SkyMiles and book our flights directly with Delta. 

My favorite cards right now to earn Delta Miles are the American Express® Gold Card, and the Delta SkyMiles® Platinum American Express Card.  You can find out all about these cards and apply for them by clicking the links below! (If you do end up using these links thank you so much! I appreciate it more than you know!)

The Cards We Used to Help Us Earn Points for Hawaii ON SOUTHWEST

This year we decided to fly Southwest to Kona from Salt Lake City. Admittedly, Southwest is not my favorite airline (don’t get me started on their boarding process) BUT we had a ton of points after earning two Southwest Companion Passes. Also, the flight time/layover to Kona from SLC was less on Southwest than on Delta. Because we earned two Southwest Companion Passes we get BOGO flights for two of us. For our family of six, flying two people for just taxes and fees (no points and no other cash costs) is pretty remarkable and makes up for what I don’t love about Southwest. 

My favorite cards right now to earn Southwest Miles are the Southwest Rapid Rewards® Plus Credit Card and the Southwest® Rapid Rewards® Premier Business Credit Card.  Because Chase is a partner with Southwest, you can also earn Chase points through a card like the Chase Sapphire Preferred® Card

and do a direct 1:1 transfer to Southwest. 

REALLY IMPORTANT: If you are clicking on the Chase links from Instagram for them to work correctly, you need to open them in a new browser. Chase blocks info and applications coming from Instagram. To do this, after the page loads, you’ll need to click the three dots in the top right-hand corner and select either “Open in System Browser” or “Open in Chrome” This will allow you to have full functionality of the info and the application.

How We Earned Our Points For Our Flights 

There are so many ways you can earn points! Here are some of the specific things that we did to earn the most that we could! 

How We Strategized For Our Delta Flights

  • Maximized the welcome bonus on one of the American Express® Gold Card (Jason applied for the American Express® Gold Card last year and received a significant welcome bonus.) 
  • Maximized our category spend on groceries, gas, and restaurant costs by earning 4x the points when using our American Express® Gold Card on these categories. (Note: We do not spend more money on groceries, gas, or date nights so we can earn points in return. We simply just make sure that when we are spending money on those things we are using the right card to earn the most points in return!) 
  • Put some of the major purchases we had that year on our Delta SkyMiles® Gold American Express Card. We did some renovations on our house, and we had a baby (hello expensive!). Instead of paying for those things with a debit card or cash, we put them on our credit card and then paid the card off right away. This means that we earned points for those big purchases! 
  • Paid for some of the flights we took that year on our Delta credit card. (We don’t use miles on every flight, instead, we book strategically to make sure we are getting the best return. So this means sometimes we pay for the flights on a card if the point redemption value is too high or not worth it. If you pay for a flight, make sure you are using the right card (not a debit card!) so you can get more miles!) 
  • We paid our cards off every month to make sure we were earning our points and staying within our budget.
  • We took advantage of the card bonuses and enrolled our cards when it made sense (for example a 5x Amazon bonus on the American Express® Gold Card came in handy when we were buying things for the new baby.)

How We Strategized For Our Southwest Flights

  • Jason and I both earned a Southwest Companion Pass and we referred each other to the cards. This gave us a HUGE chunk of Southwest points. You can get a free Southwest Companion Pass Guide here!
  • We made use of the business spend categories on our Southwest® Rapid Rewards® Premier Business Credit Card and earned 2x the points on our internet and phone bills.
  • I bought upgraded boarding times for flights to and from Hilton Head and got 4x the points.
  • We transferred 11k points from Chase to Southwest to cover one of the flights there.
  • Took advantage of the Southwest anniversary points bonus!
  • We paid our cards off every month to make sure we were earning our points and staying within our budget.
  • We took advantage of the card bonuses and enrolled our cards when it made sense.

How We Found the Best Point Redemption Value for Flights to Hawaii On Delta

When we first started looking at our dates, the redemption rates were out of control, especially through the Amex Travel Portal. We originally wanted the direct, nonstop, roundtrip flight from SLC to OGG but the mile redemption was almost 90k Skymiles per person. That was just not worth it to us. So we set up price trackers and started looking at other options. We settled on flying roundtrip from SLC to OGG with a short 1 hr layover in LAX both ways. 

After setting up price matching and watching really closely, we were able to book our 5 flights with an added infant in arms for 42k miles each. This means instead of originally giving up nearly 500k miles to fly our family to Hawaii, we were able to do it for 210k miles. That made the one short layover totally worth it!

I should note that the flights that we booked for 42k miles were $916.00 each. If we were to have paid for them, we would have spent nearly $5,000.00 just on our flights. Yikes! 

I also want to note that a 42k-mile flight isn’t that great of a deal. There are often a lot lower redemption rates for Hawaii. However, it was the best that we could find for our dates and so we went with it. If we had been able to move our hotel stay just by two weeks we could have booked those same $916.00 flights for only about 30k miles each. 

How We Found the Best Point Redemption Value for Flights to Hawaii On Southwest

Finding our Southwest flights to Hawaii was a lot easier (and cheaper) than our Delta flights the previous year. We had our dates set and I knew the itinerary that I wanted about 12 months in advance, so we watched for when Southwest released their calendar and we booked our flights the day our travel dates were released. This allowed us to get our flights to Hawaii for 11k miles.

Using Southwest, we got 6 flights to Hawaii for 98k miles total!!!

11k x 4 for our flights there (+ 2 free companion pass fliers)

13.5k x 4 for our flights home (+ 2 free companion pass fliers)

and we just had to pay the taxes and fees for all six of us ($5.60 each flight)

The current cash cost for our round trip flights last time I looked was $924.96 each, that’s almost $6,000 for our family!!!!!!

If you don’t have your dates set, then I suggest using the flexible date calendar when you are looking! If you are booking early enough and you give yourself enough time, you can get a deal that is even better than what we booked!

How We Booked Our Flights On Delta

Almost always, the very best way to make the most of a redemption booking is to do a direct 1:1 transfer of your points to the airline or hotel partner you will be using. Both my husband and I have Delta SkyMiles accounts, as well as our own Amex accounts. We knew that we were going to need to combine our points somehow. Because you can’t combine points between people, we decided that my husband would book three of the flights and I would book two of them and add an infant in arms. We then transferred the points that we needed from our individual Amex Points to our Skymiles Accounts and booked directly through Delta on each of our Delta accounts.

Combining Reservations On Delta

This meant that we had two different reservations for our family. Jason had three flights booked under his reservation and I had two with the baby in arms added. While having two different reservations for one family is kind of annoying, you can’t transfer your Amex points to someone else’s Skymiles account. So we had to book separately. 

Because we were on different reservations we needed our reservations linked. To do this we called Delta using their customer service number and had them link our reservations and then arranged our seats so we were sitting all together. From this point, we were able to check in together as if we had booked our flights together from the get-go. 

Make sure if you go this route that you call to link your reservations as SOON AS POSSIBLE. If not, you might be split up on the flight, or worse. Once we forgot to link our flights until it was too late. We had a few members of our family bumped onto a different flight and had to rearrange the whole thing. It wasn’t fun. 

How We Booked Our Flights on Southwest

I choose to book our flights on Southwest as one-way, this can be easier if there is an issue with a Southwest flight or if I need to change the reservation. I booked 4 flights there one-way, on one reservation at 11k miles each. Then I booked 4 flights coming home on another at 13.5k miles each. When that was done, Jason added one of our kids as his companion to his ticket (you select your companion beforehand, and then you just add the companion for any or all of your flights) and I added one of our kids as my companion.

My number one tip when booking Southwest redemption flights is DO NOT WAIT. Once the calendar is released (usually six months in advance)  – book them! If on the off chance, the flight cost or redemption rate does go down, you can easily request a fare adjustment or rebook if needed and get your points redistributed to your account or get a flight credit.

flying to Hawaii on points with kids
Look for the best redemption values to stretch your points and miles even further! We got $900.00+ flights TWICE for nearly free, saving our family over 10k dollars in the process!

Flying as a Family to Hawaii!

For both of our flights on Southwest and on Delta, once everything was all booked we were good to go! Each of our flights had a small tax and fee charge of $5.60 per person, each way. For our flights to Maui on Delta we paid $56.00 total in taxes (Benson was an infant in arms ticket). For our flights to the Big Island on Southwest, we paid $67.20 in taxes. Even if you consider the annual fees, we saved over $9,500 for our flights! 

How You Can Do This for Your Family!

If you want to fly Delta or Southwest, do exactly what we did! If you are wanting to fly another airline, make sure you have the right card that can transfer to your preferred airline! For example, if you want to fly United you can earn United points through a United branded card and/or transfer Chase points to United! 

flying to hawaii on points
If you want to fly another airline, just make sure that you are using cards that earn that airline’s miles or can transfer to that airline!

Common Questions About Flying to Hawaii on Points

Let’s dive into some of the most common questions about flying to Hawaii on points!

How many points do I need to fly to Hawaii?

Depending on your departure airport and desired airline, on average you will need around 20-50k miles or points to get to and from Hawaii from the continental US. Of course, this amount varies based on seasonal promotions, time of year traveling, and how early you book your flight.

How many Southwest points do I need to fly to Hawaii?

You can get Southwest flights to and from Hawaii for as low as 7k miles each way. Of course, this can also vary depending on the time of year and where you are flying from in the US. On average it is a good idea to estimate a needed 25-30k miles roundtrip.

How many Chase points do I need to fly to Hawaii?

If you have Chase Ultimate Rewards, you can easily transfer your points at a 1:1 ratio for both United and Southwest. If you are using Chase points to transfer to United plan on needing an average of 40-50k miles round trip.

How many Delta miles do I need to fly to Hawaii?

Delta participates in a dynamic pricing model which means during sometimes of the year you can book a steal of a deal! On average, it is best to plan on having at least 30-50k Delta SkyMiles for a round-trip flight to and from Hawaii.

What month is the cheapest to fly to Hawaii?

Typically the cheapest months to fly to Hawaii are October, February, and March.

How far in advance should I book my flight to Hawaii?

If you are wanting to get a good deal on your flight using points and miles, it is best to book your flights at least 6 months out in advance. This will help ensure availability.

What time of year is most expensive to fly to Hawaii?

Usually, November, December, and January are the most expensive times to fly to Hawaii because of the Holidays and families wanting to get a warm Hawaiian break.

Do you still have to test when flying to Hawaii?

No. Travelers from the US do not need proof of vacation or a negative test to fly to Hawaii.

How to Fly to Hawaii on Points Recap

  1. Have the right card for the airline you are wanting to fly. Make sure your cards either earn points for that airline or can transfer to your airline. 
  2. Find the best ways to earn points on that card. For example – welcome bonuses, category spending, referrals, using it on big purchases, etc…
  3. Search for the best redemption rate by playing with dates, layovers, and flight times. Set up a price tracker if needed. 
  4. Transfer your points to your preferred airline account
  5. Book direct
  6. Combine reservations if needed
  7. GO TO HAWAII!!! 

I hope this helps and you get to go to Hawaii for nearly free with your family soon too!




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