Reader Success: How Vic Took His Family on a Free Vacation to Portland!

Vic is a longtime reader who happens to also be a blogger.  He’s the dad of Dad is Cheap.  In today’s post he shares the details of how he booked a family trip to Portland, Oregon for almost zero dollars out of pocket!  Check out his site for personal finance advice after you read his guest post below.

Take it away, Vic!


I was a travel hacking newbie when I first read Michael’s post about how he scored a free(ish) month-long honeymoon.  As a money savings nerd, I knew it was something I had to try. I figured I could start small and work my way up to Michael’s status.

Since I started travel hacking earlier this year, I’ve scored quite a few free flights and hotel stays. Michael helped me realize that travel hacking isn’t that hard, it just takes a little bit of work and can be fun. 😉

Despite my success, I acknowledge that the whole points thing can still be pretty confusing at times.  Earning points in a program with many redemption options (think Chase Ultimate Rewards, Citi Thank You, SPG, etc.) can pay off big.  However, figuring out the best way to convert those points into a flight or hotel still sometimes makes my head spin. There can also be a lot of restrictions in redeeming the points for the flights you want.

I ran into that type of situation when I wanted to book my family’s trip to Portland during Labor Day Weekend.  There’s only airline – jetBlue – operating flights to Portland from the airport closest to my home in Long Beach.  When I realized that, at first I thought I was going to have to pay for flights with cash.  At the time, it didn’t look like there were many options for scoring a lucrative sign up bonus to book a jetBlue flight.  Though I had Chase Ultimate Rewards and Starwood SPG points, there was no reasonable way to transfer them to jetBlue.

What to Do, What to Do?

So I did a bit of research and found a high-payoff solution.  I signed up for two cards – The Capital One Venture and the Barclays Arrival Plus. Both of these cards are essentially 2% cash back travel cards in which you can use miles to cancel out ANY travel related purchases. The sign up bonuses on these two cards, once I hit the minimum spend of $3000 in 3 months, was equivalent to $460. My wife also signed up for both of these cards so between the four cards we had $1840 to use towards travel!

Booking Our Flight

jetblue-plane-airborne-360w
jetBlue was the only airline operating nonstop flights to Portland from Long Beach.

The flights from Long Beach to Portland cost $700 for my wife, my daughter, and myself. Since I only had $460 worth of travel credit on each card, I couldn’t book the flight online since I needed to split the cost between two of our cards. I had to go old school and call customer service to manually book a flight so I could use two of the cards.

It literally took me an hour as I had to call and spell out all of our names, addresses, and rewards numbers. It probably didn’t help that I made this call in the middle of the night :).

A few days after I booked the flight though I was able to redeem my miles to cancel out the $700 charge.  Success!!

Travel Hacking the Rest of Our Trip

Since I only used $700 of our $1,840 of travel credit I started considering ways to get free lodging for our trip also.  I remembered a pro tip from Michael which allows you to essentially cash out your travel credits on a Barclay Arrival Plus (and Capital One Venture). Basically, you pay for a refundable flight or hotel, cancel out the trip with your miles, and then refund your trip. You’ll end up having a statement credit on your cards. The remaining $1140 worth of statement credits paid for our Airbnb stay ($445), rental car ($152), and going out. We pretty much travel hacked the whole trip.

Vic and family converted credit card signup bonuses into free flights and lodging, enabling us to enjoy the beautiful scenery of the Portland, Oregon area without breaking the bank!
We converted credit card signup bonuses into free flights and lodging, enabling my family to enjoy the beautiful waterfalls of the Portland, Oregon area, without breaking the bank!

Cash Back Travel Cards Have Their Place

The Barclays Arrival Plus and Capital One Venture cards aren’t as popular for travel hacking as some other cards like the Chase Sapphire Reserve.  After you use the sign up bonus these cards aren’t that useful as you can get similar features on a Citi Double Cash Card that has no annual fee. But as my experience shows, there is some serious value in signing up for them. If you have a spouse, it’s an easy $1840 in sign up bonus.  And of course you don’t have to sign up for them all at once.  For people who don’t want to figure out points and travel partners, these cards might be right up your alley.


Notes from Michael: Thank you, Vic, for sharing your experience!  It’s always great to read success stories!  You mention being a novice not that long ago but you’re definitely up to speed now.  Nice work getting resourceful and not taking no for an answer immediately.  As you pointed out, the beauty of Arrival Miles and Capital One points lies in their versatility.  Though you may not get four or five cents of value per point you can sometimes make up for it in saved hassles!


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Are you “cashing in” with independent credit cards?  Have some Portland stories of your own?  Share your thoughts in the comments below!

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2 thoughts on “Reader Success: How Vic Took His Family on a Free Vacation to Portland!

  1. Thanks for featuring me MIchael! You helped me a lot on figuring out this whole travel hacking game.

    That protip on essentially cashing out the sign up bonuses definitely makes these cards worthwhile as they’re an easy $1840 for four cards (as long as you have a spouse). You also wrote that it’s possible to churn the Barclay card so I’ll try that in a few months and see if I can get the sign up again. I’m currently working on Bank of America’s travel card which is worth $200.

    That Chase 5/24 rule is killing me! As you know a lot of the good cards are Chase but I’m ineligible for the new Chase Sapphire Reserve. I even tried going to a branch but that didn’t work in my favor. ¯\_(ツ)_/¯

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