How we flew to Hawaii for FREE!

Updated: Oct 20, 2019


Last year my husband and I took our first tropical vacation to Los Cabos, Mexico. After this trip we were hooked and decided that we needed to make traveling a priority in our lives. We began trying to decide where to go next. Since we were trying to conceive it really narrowed the list down to only a few places that didn't have the Zika risk. Hawaii made the top of the list. We decided it would be the perfect spot for our 2019 trip, which ended up turning into a baby-moon!

When we started looking into the cost of the trip, we discovered it would be about $3,000 for a 7 day 6 night trip to the island of Oahu. Plane tickets alone would be $1000 and Hawaii is not like Mexico where food, lodging, and transportation is fairly inexpensive and negotiable. Everything is expensive in Hawaii!

$3,000 seemed like so much money to spend for a 7 day adventure so my husband and I started looking into different ways we could help lower the cost. We began researching travel hacking since we'd read about so many people having success with it. HERE is the Choose FI Podcast episode we discovered that started it all.

When my husband and I first listened to the podcast we thought, "this will be easy, we just sign up for a few credit cards and then bam our trip is paid for." It just seemed like such an easy way to earn a free trip. Well, are you ready for the truth?

I'm going to be straight up with you, we are a year into travel hacking and with 1 trip down we have learned a ton! I'm here to tell you that there is a learning curve to travel hacking and we did make a few mistakes along the way. You WILL have to do your research, you WILL have to read ALL the fine print, and you WILL have to stay on top of your finances in order to have success. However, it's a pretty simple way to earn free travel without putting in a ton of time outside the home.


Is it's really worth it all the research and hassle? Heck Yes! Although we did not cover the full cost of our trip this time around we did save about $1,800.

Check out the full expense sheet HERE.

We have overcome some of the beginning obstacles and I'm here to share with you step by step how we covered the majority of our trip with credit card points and rewards.


First off there are a couple things you need to understand about the process.

#1 - You must budget your money. If you currently have credit card debt DO NOT TRY THIS! Take some time to get all consumer debt paid off and get a good budgeting system in place and THEN come back and learn more.

#2 - You need to plan ahead. I would give yourself at least a year to cover the cost of a trip like this for two people with rewards.


I determined that I needed about 45,000 United points per person in order to fly to Hawaii. I also wanted to cover some of our activities and hotel costs so I looked for a card that offered good rewards that could be used for multiple purposes.


The first card we signed up for was the Chase Sapphire Preferred Credit Card*. My husband signed up for this one. This card offered a 50,000 point bonus for spending $4,000 in the first three months of opening the card. The cool part about these bonus points is that they can be used in many different ways like the following.

- Points can be cashed out, 1 point = 1 dollar, so 50,000 points is equal to $500.

- Points can be transferred to a Chase Partner. Chase has a whole list of partnering hotels and airlines that you can transfer your points to, like United and Southwest.

Example: The 50,000 Chase points could be transferred and used as 50,000 United points.

- Points can also be used in the Chase Ultimate Rewards Portal for hotel nights, car rentals, experiences, and more. This is the best option in my opinion because you can get the most value for your points.

This card really was, and in my opinion, still is one of the best travel rewards cards because the points are so versatile.

Now spending $4,000 in three months** for my husband and I was not an easy task. We have pretty low spending on a month to month basis so we needed to correlate opening this card with a big expense that we had coming up. You may need to do the same. This is why I highly recommend budgeting and planning out your three months before you open the card. Otherwise you will end up spending more than you would normally spend just to get the bonus.

After the three months we did it! We hit our minimum spend, BARELY, and we got the bonus. If you're coming up to the end of your three months and you're close I would highly recommend giving Chase a call and asking them if you are on track to hit the minimum spend. They are super friendly and will let you know where you stand.

*The annual fee for this card is $95 but typically it is waived for the first year. Occasionally they will offer 60,000 points for a $4,000 spend however, the annual fee is not waived. They basically just give you an extra $100 in points and make you pay the fee.

I will be sharing referral links in this post. By clicking on the link and signing up for a card through my link I will get bonus points. Once you sign up for a card you can also get a link to share with friends/family. If they sign up you will get a bonus.

**The three month period is really more like 2 months and 2.5 weeks since you have to wait 7-10 business days for them to ship you the card.


You obviously don't want to spend more then you normally would in order to hit a minimum spend requirement. This will throw off your budget and is not going to benefit you in the long run. One thing that can help if you're close is to buy a gift card with the credit card. This will allow you to hit the minimum in the required timeframe and then you can use that gift card over the next few months.

Now when I say to buy a gift card I don't mean to go out and buy a gift card to your favorite steakhouse. I also would not buy a ton of gift cards just to hit the minimum spend requirement. But, if you're a few hundred dollars away you can buy a gift card to somewhere that you normally shop for everyday expenses, like Walmart, Amazon, a gas station, or your local grocery store. (We shop at a store called Winco because they are the best place for groceries in our area, however, to keep costs low they do not accept credit cards. One way around this is to buy a Winco gift card through their website which you can purchase with a credit card.)


The next card we used to gather rewards was the United MilagePlus Credit Card* through Chase which I signed up for. This card offered 40,000 United points for a $2,000 minimum spend in 3 months. This minimum spend was much easier for us to hit and we could just put typical monthly expenses on the card in order to receive our bonus.

You're probably thinking that 40,000 points doesn't seem like enough since we needed 45,000 to fly to Hawaii, I will go into how we got the addition 5,000 next.

After collecting the 40,000 points I had my husband sign up for the same card (this next part is important because we each needed an additional 5,000 points to have enough to cover our flights). When my husband signed up for the card I had him do it through "My Referral Link." By doing this I was rewarded 10,000 bonus points. Which put me at a total of 50,000 United points and my flight to Hawaii was only 45,000. So my flight was covered.

Now for my husbands flight. He hit his minimum spend and was awarded the 40,000 United bonus points. Since he put $2,000 on the card he also got 2,000 points rewarded (this card offers a 1:1 point per dollar reward) which meant he needed 3,000 more points in order to have enough for his flight. This is where that Chase Sapphire Preferred Card came into play. We were able to transfer 3,000 Chase Ultimate Rewards points to United and they became Untied points. Which put him at 45,000 points and his flight was now covered.

*The annual fee for this card is also $95 but again typically it is waived for the first year.


- You can only transfer Chase Ultimate Rewards Points to a partner like United in 1,000 point increments.

- You can only set up one reward account per partner with your Chase account. So my husband can transfer Chase points to his United account as often as he'd like but he cannot transfer his Chase points to my United account. That is why it was important for me to sign up for the United card first and then refer him. That way I had enough points through United and he could transfer his Chase Ultimate Rewards Points to make up the difference he needed.

- It can take a few business days for the points to transfer so make sure you plan ahead. In my experience they transfer from Chase right away or within a few hours, but it took a few days for the points to become available to use on the United end.

- Once points are transferred to a partner you cannot transfer them back to Chase so make sure that you only transfer the amount you need (in 1,000 point increments) and make sure not to transfer them until you are ready to use them.

- You will have to pay for the 9/11 security fee out of pocket. This cost was $5.60 per flight (may vary depending on location). So between my husband and I and our 2 flights we paid a total of $22.40 to fly to Hawaii.

- Since my husband and I each had separate accounts we had to book 2 one-way flights from each account in order to sit next to each other. Here's how that looked:

He booked 2 one-way tickets from his account from Idaho to Honolulu for 45,000 points and $11.20 security fee. Then I booked 2 one-way tickets through my account from Honolulu to Idaho for 45,000 points and $11.20 security fee.

- One mistake we made when booking our flights was not paying for the security fees with our United cards. One of the benefits of the United Card is that you get 1 free checked bag with your flight. However, you cannot get the free checked bag unless you book the flight using your United credit card. This was a surprise to us at the airport when we were checking a bag and they charged us $30 for it. Luckily we only had one bag but we ended up paying $60 total for that one checked bag that could have been totally avoided had we booked the flights using the United card. Learn from my mistake... read the fine print.

- You need to make sure to book your flights at least 30 days in advance if you plan to use reward points with United.


Now you're probably wondering what we did with the remaining Chase Ultimate rewards points. We split it up a few different ways and used them for a few excursions and free hotel nights. We ended up booking them all through the Chase Ultimate Rewards Portal and saved a ton money! Check out my Hawaii trip spread sheet HERE to see the breakdown of everything we spent out of pocket and everything we were able to cover with points. We also went on this trip with another couple and I will show the cost of things that we split with them.


Was it all worth it? We saved a ton on this trip and since we saved so much we were able to splurge on a few things. One night we stayed at a really nice resort on the North side of the island. This night cost us about $270 which is not something we would typically do but since we saved so much money in other areas we were able to treat ourselves (Treat yo'self) to one fancy night. This totally made it all worth it. Plus now that we have gone through this process once we have a pretty good system down for managing our credit cards. We have learned that if you have any questions just make a call to the credit card company and/or read the fine print. All the terms are written pretty clearly and if you take a little extra time understanding them it makes everything run smoothly.

Now that we've gone through the process and have learned from our mistakes I know that we could have covered more of our trip with points instead of dollars. This is exciting because I'm already gearing up and planning our next big adventure!

Make sure to SUBSCRIBE so that you are updated with future posts on how much we save on the next trip.


What about the 5/24 rule?

When opening credit cards there are a few things to keep in mind. Credit card companies will not let you just open an unlimited amount of cards. They do have some rules that you have to follow and with Chase cards you need to make sure you understand the 5/24 rule before starting.

A brief explanation is that each person can only open 5 cards in a 24 month period. This also includes being added as an authorized user. So if you're doing this with a spouse I would highly recommend not adding each other as authorized users as this will affect you both and you will hit the 5 cards much quicker.

HERE is a great article by The Points Guy where you can read about it in more detail.

Won't opening and closing cards hurt my credit score?

Now I cannot speak for you since I do not know all the variables that affect your personal credit history but I can tell you that this has not affected my overall credit score in a negative way. I have watched and tracked it every month to see the changes and to see what exactly it has done. It does go up and down every time I sign up for a new card but overall it has actually helped my credit score. This is normal from what I have researched.

If this is something that you're worried about I would highly recommend you do more research as to how credit scores work and what things hurt and help them.

Where can I learn more?

There are so many great resources out there with more information on travel hacking. Here are some of my favorites:

The Points Guy - This website is ridiculously informative and they are always releasing great articles that go into depth on many travel topics.

Kara And Nate - I learned about the luxury of the airport lounge from these guys. One huge benefit the United MilagePlus Card offers is 2 one-time access passes to the United Club lounge. We took full advantage of these during our layovers in San Fransisco on this Hawaii trip and let me tell you it is pretty life changing to have a nice quite place to relax while waiting for your connection. There was also great food in the lounge, THAT IS FREE, which was a lifesaver for me since I was 27 weeks pregnant on our trip and I'm way too cheap for airport meals.

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