How We Traveled for Free this Fall

This article is going to give you the quick and dirty of how my family of four took a five-day vacation to Mexico this fall for free. That’s right we were able to completely pay for our trip with hotel points and miles. Yes, that does take money on the front end, however, we were able to leverage our everyday spending on groceries and bills into a great vacation.


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I had grand plans for us to travel to Hawaii. Covid squashed that plan. We had opened a Southwest Chase Visa card to help earn miles and help reduce the cost of flying. You can sign up for the card I have here. The sign-on bonus can change from time to time so I would keep an eye out for anything over 50,000. Responsible spending and a great bonus gave us a large chunk of miles. I was able to combine the bonus and everyday spending to earn a companion pass.

The companion pass allows one person to fly with you for free to any destination for only the tax which is $5.60. Once you earn this pass it is good for the remainder of the year in which you earned it and the entire next year. I used this pass to cover my husband’s airfare to Mexico. The rest of us paid 42,000 x3 for round trip tickets to Cancun from Tampa.


For accommodations, we had decided to remain brand loyal. We have picked the Hilton Brand of Hotels. We love the variety of Hilton’s in the Orlando area and their proximity to Disney. You can read about a few of them here and here. We also used a Hilton Branded American Express Card. Again, with a generous sign-on bonus and features like 12x points on groceries we were able to squirrel away enough points for a big trip.

When you book four nights with Hilton points you get the fifth night free. We were able to book five nights at the brand new Hilton Cancun All Inclusive from 380,000 points. Now, before you think this will take forever it only took us one year!

Leveraging your responsible everyday spending into hotel and airline points and miles can lead to amazing adventures. Check out the post on our Mexican vacation here.

Let me know if you have any questions! Do you travel with points and miles?

I'm Jen. Disney Lover, runner, penny pincher and mother of two boys, We live a few short hours away from Orlando and try to visit often. Follow along for family and adult Disney adventures as well as the occasional non -Disney family adventure.

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