How I Travel For Free, Pt. 3

In this post, I’ll be reviewing the strategy I employed in 2016 in order to obtain the travel benefits I mentioned in my previous posts. I’m not an expert at travel hacking nor do I claim to have any real knowledge. Everything that I know about travel hacking comes from I highly recommend this site to anyone interested in wanting to learn more about travel hacking.

Without further ado, here is the spreadsheet I developed to help me keep track of the credit cards I’ve opened in the last 2 years. Note how my credit score was mildly affected. However, as of December 2017, my credit score has bounced back up to 816. Who says opening multiple credit cards will hurt your credit card? πŸ˜‰

Travel Card Spreadsheet.png
Credit Card Spreadsheet (Jan 2016 – May 2017)

To be honest, I’m just picking the low hanging fruit here when it comes to credit card rewards. Some people apply for 10-12 credit cards in a single year and have devised a well thought out system on how to maximize their points. Perhaps one day I will reach that level of expertise, but the points I’ve accumulated with these cards have provided me with more than enough satisfaction for my travel needs.

Reward Points.png
Summary of the points and cash I’ve accumulated with my credit cards.

The acquisition of the aforementioned points have allowed my wife and I to travel to the following destinations from March 2016 to December 2017.

Trip Itinerary 1.png

All of our domestic flights were free courtesy of the points I accumulated on my Chase Southwest credit cards. When you reach the 110,000 point threshold, you automatically qualify for the Southwest Companion Pass, which is basically a buy one, get one free pass that’s good anywhere between 1-2 years, depending on the time of year you qualify for the pass (more on this in a later post). The great part about qualifying for the pass is that you don’t have to use 110,000 points to get the pass. The fact that you get to the threshold means you are given the pass FREE. In other words, you actually have 110,000 points to use at your disposal while also bringing along a companion to travel with you. How amazing is that?!

Trip Itinerary 2.png

The Chase Ultimate Rewards program is, in my opinion, the single greatest travel rewards program available due to the flexibility of the points that can be use with Chase’s affiliate travel partners. Furthermore, you can directly book flights and hotels on Chase’s Ultimate Rewards’ website. The best part about the latter is that you’re entitled to 25% off if you book directly through the site.

So, you either use your points directly on the site for a nice discount or you can search Chase’s affiliate partners’ websites to find a better deal. All you would have to do in order to redeem your points for travel through an affiliate is transfer your points from Chase’s website to the affiliate website.

I’m a little saddened that we are coming up to the end of our companion pass. It’s set to expire at the end of the month and now we’ll no longer be able to travel the way we have been the last year and a half. We made a mistake during this process in that my wife got a Southwest Plus credit card over a year ago, not realizing we should have waited until September 2017 to apply for both the Southwest Plus and Southwest Premium in order to “re-qualify” for the companion pass but under her name instead of mine. Oh well. I guess that’ll just mean we’ll have to get more creative with which credit cards to apply for in the coming year in order to continue traveling at a discounted rate or even better, free.

I’d recommend the following 4 credit cards to get started as they provide a great introduction to the world of travel hacking. They’re easy to use and very convenient for you to be able to book your travels.


1. Chase Sapphire PreferredChase Sapphire Preferred.png

2. Chase Ink PreferredChase Ink Preferred.png

3. Chase Southwest PlusScreen Shot 2017-12-23 at 9.43.33 PM.png


4. American Express Starwood PreferredAmerican Express Starwood.png


2 thoughts on “How I Travel For Free, Pt. 3

  1. I don’t believe that you touched on the yearly fees after the first year. From your chart it looks as if you have nearly $700 in fees per year after the first year with all those travel cards… what are your thoughts on this? Won’t this high yearly fee essentially catch up to you as the years go by for the “free” travel you earned in the first year? Thanks, Mike.


    1. Hey Mike –

      That’s an excellent question and one that I was thinking about how to incorporate in my posts, but ended up deciding against it. The reason being was because I wanted to emphasize the idea that one could take advantage of what the credit card rewards system has to offer without it adversely affecting your credit score. You’re absolutely right in that it’s not 100% free. A more appropriate title whether in my posts or other travel hacking posts would “How to qualify for travel subsidies using the credit card rewards system.” Thanks for pointing that out and giving me an opportunity to respond to that glaring question. I’m going to bullet point my responses to your inquiry. Bear with me:

      $700 credit card fees the first year: The actual tally is ~$601. However, you’ll notice on my spreadsheet that in the first year, 3 of those cards don’t asses a fee, so in the first year alone, the total fees assessed is $358. You’ll notice that there’s a “Downgrade Option” column. What you have to do is downgrade your card before the first year of owning that card arrives, so that you can avoid being assessed the annual fee. Regardless of whether you decide to downgrade or cancel your credit, you will still have access to the points you’ve accumulated from the credit card reward programs. My wife and I basically take turns every year (or 2, depending on the criteria set forth by the credit card company) applying for the aforementioned credit cards, so that we’re collecting the same (or a similar) amount of points in perpetuity.
      The valuation of points differ on a monthly basis and differ by each credit card issuer. To be reductive, the point valuation ranges anywhere between 1-1.7 (pennies) : 1 point. On top of that, each credit card company sometimes issues specials or, like the Chase Ultimate Rewards system, you can obtain a 20% “discount” if you book through its system. You couple all of these and compare that with the $358 you paid in fees and it’s quite clear, you come out ahead in a big way…especially if you have the Southwest Companion Pass in your possession.
      The fact is we all spend money, but the idea behind travel hacking is to subsidize your travels if you’re methodical about how you utilize and employ credit card spending. Sure, I’m not really traveling for free, but it’s far greater benefit if I’m able to travel at a significant discount. At least that’s the illusion I’m telling myself. πŸ˜‰ Thanks for the inquiry.


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