The Free Hawaiian Vacation Part I – Intro and Flights

We went to Hawaii for our honeymoon and the hotels we stayed in and the first class airfare to and from the islands were totally free, exclusively through the power of credit card bonuses!

Now, to be clear, our Hawaiian vacation was decidedly un-free. We spent a lot of money doing things like learning how to SCUBA dive and how to fly a plane around the island of Kauai (That was supremely cool and absolutely crazy! Why did they let Mr. Chedda do that?!) 

But the big ticket items—the flights and hotels—were totally free to us!

Getting Started

The tiny Cessna that Mr. Chedda flew us around Kauai in
The tiny Cessna that Mr. Chedda flew us around Kauai in

When Mr. Chedda and I first got engaged, we decided within a few weeks that we wanted to take a big trip to Hawaii after the wedding. Neither of us had been to Kauai or Maui, we hate the cold, and the islands looked really, really awesome. We also knew that we wanted to make the trip longer than a week so that we could really savor it and not be distracted by the sense of impending doom thought of returning to work from our tropical paradise.

Prior to honeymoon planning, we had only dabbled a bit in credit card churning. I’d gotten a pair of Southwest cards to earn us a two-year Companion Pass, we’d each gotten a Chase Sapphire Preferred card, and Mr. Chedda had gotten a Bank of America Better Balance Rewards card to get us free Netflix every year. We were thrilled with the ridiculously sweet free stuff we had gotten thus far, but it turns out that was some piddly minor league ish compared to what we would accomplish over the coming year.

In all, between April 2015 and August 2016, we earned more than $10,000 worth of credit card bonus goodies that let us take what will probably be the most luxurious vacation of our lives.

The Flights

The Chedda family eating warm chocolate cookies and drinking wine and iced orange juice in our free first class seats
The Chedda newlyweds eating warm chocolate chip cookies and drinking wine and iced orange juice in our free first class seats

Mr. Chedda and I are infrequent fliers and picky sleepers, so we knew that to make a flight as long as the one to the Hawaiian islands worth it we would need to get some comfortable seats. This may be what started our minds on the path of churning our way to a fancy vacation–we wanted first class seats but definitely did not want to pay for them.

A round-trip first class flight from the contiguous 48 United States to Hawaii was worth 75,000 American Airlines (AA) miles when we were booking tickets in 2015 (now it’s been bumped up to 80k). An island hopper flight between Maui and Kauai was 10,000 AA miles. So, Mr. Chedda and I each had to have at least 75,000 + 10,000 = 85,000 AA miles in order to cover all of our honeymoon flights.

The easy choice for racking up AA miles was the Citi AAdvantage Platinum Select World MasterCard. Each of us got 50,000 miles for picking one up in April 2015 and the annual fee was waived for the first year.

We bided our time until November, when Citi inexplicably mailed us special offers inviting us to apply for the same exact card again, this time for a 60,000 mile bonus. What? Citi’s marketing department may not be the most on top of things. Again, we applied, spent the required $3,000 each, and Citi handed us our free air miles.

So, where does that leave us? It leaves us each holding over 50k + 60k = 110k AA miles, enough for all of our honeymoon flights plus more! It also put us almost exactly 331 days in advance of our planned trip, which is exactly the time frame that American Airlines opens up their award seating for purchase! Boom!

The rest of our flight plan fell into place quickly: 330 days in advance of our planned departure we booked one way first class tickets from DC to Maui (75k AA miles for the two of us). A week later, we booked our interisland flights (20k AA miles). And finally, another week after that, we booked our first class return flights to DC (the final 75k miles)!

The Money

Each leg cost each one of us $5.60 in unwaivable customs fees, which put us back a total of $33.60 for our six first-class transcontinental tickets. We checked two bags, which were free with our first class tickets. If we had paid cash for these exact flights instead of using points, it would have cost us over $5,000. And some googling tells me that even taking economy flights would have cost us $1,500 at the very least.

 Cost to usPotential costSavings
Fancy option$34$5,000$4,966
Basic option$34$1,500$1,466

Almost a year after booking our fancy flights, we hopped in a giant metal bird to be shipped across the sky and plied with champagne and free food.

To this day, I’m in awe that this worked! I can’t believe how much free stuff credit card companies will give responsible credit users. For an organized, financially responsible human who’s willing to put in some time to research this stuff, the fruit is pretty low-hanging and the profits are incredible. I recommend the churning and award travel subreddits as excellent resources for getting started with credit card rewards and churning. The people there are really helpful and aren’t paid (although sometimes they can receive a referral bonus) for helping you out or recommending stuff, so their incentives are structured in your favor.

Running total of Money Spent: $34*

Running total of Value (conservative): $1,500

Running total of Value (actual value): $5,000

Leftover bonus: 40k AA miles

*Sometimes when I calculate the value I get from a credit card bonus and what I spent to do it, I have to work in the opportunity cost of the spending I did to get a bonus. Usually, the money we use to complete the minimum spend for a card could have been spent on a cash back card that would give us 2% back in rewards. Thus, for each $100 spending you do to get a bonus, you lose 2% x $100 = $2 in opportunity cost. However, when we made the plan to churn credit cards for our honeymoon we specifically forced ourselves to do it while still putting our normal spending on cash back cards. We went out of our way to find creative ways to spend the minimums, like asking family if we could pay for their flights, or placing six calls to our wedding venue to ask if they would waive their “checks only” policy just for us. Since these are not things we would have done without having a credit card bonus on the line, we consider our opportunity cost to be $0. For more tips on how a frugal person can deal with minimum spend, Go Curry Cracker wrote a useful blog post on the topic.


Would you try or have you tried churning credit cards? What do you think?

2 thoughts on “The Free Hawaiian Vacation Part I – Intro and Flights”

  1. I really appreciate the footnote at the end of the post. The thought of not using my cash back credit cards is the primary reason holding me back from churning. Thanks for the info! We are planning a trip to Ireland in 2018, so hopefully this will help.

    1. Nice! And churning doesn’t have to be an all-out thing. You could totally just get one or two bonuses that would be helpful to you, close the card(s), and never think about churning again!

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