Reader Testimony: How I (Almost) Flew to South America in First Class for Free

The following is a guest post from Jason Jacobs  He is a web programmer working on becoming a missional entrepreneur in small business website design and SEO. If you need a website or SEO work, he can help. Check out the free website promo he’s offering to Help Me Travel Cheap readers.

A year ago, I thought playing the miles game was a joke. In two weeks, my wife and I will be flying in first class for the first time ever, and it only cost me $20. In a moment, I’ll tell you how I did it.

In fact, I was almost able to score first class international tickets on only miles. The only reason I didn’t was because I needed to buy two tickets (for my wife and me), and I was a mere 36K miles short. (I’ll tell you how to fix that too.)

All this from a guy who actually had the audacity to submit to Craig a post where I said earning miles is a joke.

The “traditional” state of mind

Let me briefly recap why I didn’t think the miles game would work. I thought getting multiple cards would hurt your credit score, and to me that was the most important thing to keep solid for my financial future.

The way I saw it, the only way you could get airline miles was flying a lot or purchasing a lot with your miles card. If you were smart, you’d get a card that had bonus miles for certain purchase, like the Chase Freedom does. I thought the best thing for me was to get a card for the airline I used the most.

In my mind, the only way to get a bunch of miles was to spend a lot of money.

I was just ignorant, and I kick myself for not seeing the light sooner.

How I became a player

After I submitted that post to Craig, he graciously and completely disagreed with me and wrote a rebuttal later in the week. In my defense, I didn’t know about Help Me Travel Cheap, but I sure had egg on my face. He made it look so easy.

I decided to start with the Chase Sapphire card and found it really simple to spend the minimum *without* making unnecessary purchases (essential to this game, but I’ll get to that later). Within three months, I had 50K points without breaking a sweat.

Under my previous mindset, I got a United Card with bonus miles, and I had purchased tickets and some other higher-dollar items with it. Combined with the Sapphire, I had 104K miles to play with.

I downloaded Craig’s guide “How to Travel Anywhere in the World For Free” to make sure I had everything I needed to start my hunt. I wish I had downloaded it sooner. I’d have applied for at least one more card, and my trip would have been much cheaper (re: free).

I also took advantage of Craig’s travel free coaching. He was really patient with me and gave me several different options that would work. Especially if you’re planning a miles-based trip for the first time, you should get in touch with him.

We almost got to Paraguay on miles alone

I mentioned a bit ago that I was only 36K miles short of getting two round trip tickets from Richmond, VA to Asuncion, Paraguay. Some of that would have been in first class.

The flights were only 70K miles a piece. I poked around the website looking for the best itinerary, but I couldn’t find one that suited us. I was going to have to buy one outright and use miles for the other.

With a little thought, I’d have seen the solution. I could have downgraded my Sapphire Visa to a Freedom (and also be able to take advantage of the 5x miles bonuses on things I already buy) and then applied for a Sapphire MasterCard. That would have gotten me 40K UltimateRewards points that I could have transferred to United, and I’d have had enough for two tickets to Paraguay. The longer of the two legs would have been in First Class.

Just a couple words of advice

This is turning out to be a really fun game. It feels like you’re beating the system, and who doesn’t love to feel like they’re sticking it to the man? The unfortunate truth is the credit card companies hardly give us a notice; they’re too busy making money hand-over-fist on people who don’t know how to use credit cards properly.

I’d be remiss not to pass on a couple words of caution if you’re going to start playing.

  • If you currently have credit card debt that you don’t have control over yet, this game is not for you. Pay it all off or at least develop and stick to a plan to pay it off as soon as possible. The last thing you need is another credit card.
  • While you’re spending to complete your initial requirement, make sure you pay off what you charge. I track every dollar we spend in our family, and credit card purchases are treated like cash. They get deducted from the budget and paid in full every month. That was a huge paradigm shift for me, because I used to use credit cards for purchases I didn’t have money for. Don’t fall into that trap.
  • Cancel your card before you reach the anniversary. Craig offers some tips, like setting a calendar reminder for 11 months after you activate the card. That way you’ll get your bonus points without having to pay the annual fee. Just make sure you have an active card that you can transfer those miles to.

How far can you go without paying a dime?

Even though I didn’t book the whole flight on points, you can see (and I can now, too) how easy it would have been to be able to do so. In the end, we decided to fly out of Miami (about half the price of tickets out of Richmond), and to get to Miami I used some points. I could have saved them for our next trip, but we wanted to have some spending money here.

To get to Miami, I used 70K points – total, for two seats – and $20. When we go back to Richmond, we’ll be flying first class.

We’re coming back to Paraguay in two years at the latest. Next time, I don’t plan on paying for tickets.

If you play it right, you can fly for free (only paying taxes). How much will you pay for your next trip?


  1. says

    Our mother/daughter trip to Europe this summer was only $206 out of pocket for two round trip tickets in coach – buying those tickets in cash would have cost about $1,950!

    I didn’t have enough points for business class, because I got the BA VISA that gives you 50k points at your first purchase and 50k on your first anniversary, and even with the full 100k it wouldn’t have been enough. (I filled in the missing 30k with transfers from UR).

    But now that I’ve depleted my Sapphire VISA UR points, does the downgrade and then reapplication for the Mastercard version really work/ is it fairly simple? UR are so versatile – I’ve transferred them to Southwest/Airtran and to British Airways so far. It would be great to have more than the measly 9k in my account right now.

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