How we’re getting 3 people to Hawaii and back for free

Before I jump in, please don’t think I’m trying to brag.

There are travel hackers out there who I’m sure could get way better value out of their points by using them to somehow get 1st-class tickets, along with a free stopover in Sydney, for the same price.

We’re flying coach, and we’re psyched.

Get on with it, so how?

American Airlines has really good prices on flights to Hawaii right now.

For example, you can fly from Atlanta to Maui for just over $500 RT:


For two of us flying out of the Bay Area, we used Citi ThankYou points I earned from getting the Citi Prestige credit card last year.

Though it’s ending in July 2017 (here’s more about the devaluation), Citi has had a partnership with American Airlines that makes ThankYou points worth 60% more if you use them on AA flights.


So instead of using my 50k-point Prestige bonus on $500 cash, we used them on ~$800-worth of AA flights to and from Hawaii.

Luckily the flights were the same cash price in Citi’s travel booking portal as they were on Google Flights, which meant we could get two round-trip tickets for right around 50k ThankYou points.

One weird thing: 

For some reason the flights costed a lot fewer points when booked as two different one-way flights, instead of as a round-trip.

If anyone knows why that is, please let me know.

Here is what a one-way costed for one of us:


A couple of cool things about using ThankYou points instead of American Airlines points to book our flights:

  1. You need some luck to use American Airlines miles for a good price within your travel dates. Booking through the Citi portal means any date/flight can be booked with points, and the points price directly correlates to the cash price, meaning you can take advantage of fare sales.
  2. Because we booked with ThankYou points, we get to earn miles on our flights instead of spending them. Because Alaska Airlines awards you miles based on the distance you fly instead of how much you pay, I’m planning to credit my flights to my Alaska account rather than my American Airlines account (I think you can do that?).

The next step was getting a best friend from Tampa to Maui to join us.

Since I had only 5k ThankYou points left, I used those and $199 to get her from Tampa to Maui.

Because the Prestige card gives you a $250 travel credit every year, that $199 will get refunded to me.

Citi lets you pay in whatever distribution of points/dollars you want:


We initially thought she’d be flying out of Atlanta, not Tampa.

Because I was out of ThankYou points, I used 22.5k American Airlines miles to book her ticket from Hawaii back home.

We lucked out that her travel date happened to be one of the few affordable dates into Tampa:


There you have it.

We’re getting three of us to Hawaii using only the points/miles from one and a half credit card sign-ups (there are several different credit card bonuses offering 40-60k AA miles).

Good deal? Where did we go wrong? Let me know!

One thought on “How we’re getting 3 people to Hawaii and back for free

  1. Pingback: Check out the mistake that cost me 2ok AA miles | easyjourneys

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