That Time We Thought We Were Travel Hacking

That Time We Thought We Were Travel Hacking

My wife and I had an awesome honeymoon. It was a 4 day concert at an all inclusive resort in Mexico, bookended with extra nights at the resort on either side. We spent a little over a week in January enjoying warmer temperatures, great music, fun excursions and more Coronas and Pina Coladas than I ever want to drink again. We enjoyed it so much that we made a goal to celebrate our fifth anniversary by doing the trip again. We started putting away $50 a month into a “five year honeymoon” fund.

As the years passed, a few things happened. We began to realize that going on a trip for more than a weekend without our (now plural) children would be a huge ask from other family members and the logistics of it all weren’t going to fall neatly into place. We also began to want more than just sitting at a resort, listening to music and occasionally getting out for a guided tour. We thought about places we could visit where we could actually go out of our comfort zone and… have an adventure.

We had always enjoyed hiking and being outdoors and camping when we could, so a big ticket item for us was getting out to some National Parks out West. Living in Pennsylvania, we knew that it was going to be a long drive to get to where we wanted to be. The combination of traveling with small children, being limited on vacation time and not wanting to put extra wear and tear on our family vehicle led us to a better solution – flying.

We were planning the trip about a year and a half out so we had some time to plan things out carefully. We found out about the Southwest Rapid Rewards Premier credit card. The deal at the time was that we would earn 50,000 Southwest Airlines Rapid Rewards points if we spent $2,000 in the first three months. We looked at past spending on our credit card (we only had one at the time, a basic no annual fee card that I had since I was a teenager) and quickly realized that just by charging a few of our monthly expenses at the time we could easily hit the minimum spend. Beyond that, our historical credit card spending projected out would help to get us to over 70,000 points by the time that we needed to book our flights.

We opened up this card back in early 2015 to help defray expenses for a trip in mid 2016. We easily hit the minimum spend (the total spending that you need to hit to get the signup bonus points) and used this card for most things that we would normally use a credit card for going forward.

The result? The flights for our family of 5 were going to run us $1,600 (our youngest was under 2 at the time, so she flew on our lap for free) for 4 round-trip fares. We were able to redeem our points for 2 round-trip fares and another one-way; leaving us with 3 of the total 8 fares to pay for with cash. We spent $600 getting the other fares, saving us $1,000 total.

We saved $1,000 just paying for the things we normally paid for with cash – groceries, telecom bills, insurance, gasoline, etc. We didn’t do anything illegal or illicit or even any sort of “manufactured spending”. Our reward for simple intentional spending – $1,000 less that we needed to spend to go on a trip that we were already planning on.

Upon reading (and listening) to many more strategies to use credit cards and rewards points to save on travel, we realized that we could have opened different cards and saved more money in the long run. But did we need to? Nope.

The Simple Path to Travel Savings

Jim Collins (creator of the excellent Stock Series over at has often stated that low cost index funds are the simple path to wealth. For the vast majority of smart investors, they are. Some folks have the time, patience and intestinal fortitude to pursue individual stocks in a buy and hold fashion. These people may have the skills to read SEC filings and company press releases and read between the lines. These individual stock investors may outperform the returns of a total stock market index fund, they might not. Most people can come close enough with an index fund to not justify the extra time spent researching specific individual stocks.

I like to think of the Southwest cards as the index funds of travel hacking. Do I really want to look at saver availability or travel alliance partners for the rewards points that I have? If I am just getting started, probably not. Southwest flies to nearly all major metropolitan areas in the United States, and also a handful of destinations in Mexico and Central America.

Our usual situation is that we like to take a big trip every year or so to somewhere in the US that we haven’t been to before. Paying cash for our flights would easily be one third of our total trip expenses. Knocking the price of the flights to $0 (you do have to pay a $5.60 tax for each fare but that’s peanuts) is a gamechanger for our family of 6.

The Companion Pass

This strategy becomes supercharged when you are able to acquire the Southwest Companion Pass. In short, this allows you to designate one person to fly with you for free (other than the aforementioned $5.60 September 11 Security Fee ) for the remainder of the calendar year in which you earned it, and also the next calendar year after that.

You can earn it by flying 100 times in a calendar year or by earning 110,000 Southwest Rapid Rewards points in a calendar year. The former is not a likely scenario for most and the latter, while daunting, can be accomplished by getting signup bonuses for two of the three Southwest credit cards currently offered by Chase. The best part about this is that earning the SW CP doesn’t cost any points. So by the time you earn it, you have free travel for your companion AND 110,000 points to spend.

I plan to write a follow-up post going more in-depth on the best way to earn the Companion Pass but being able to get nearly free travel for one person for 2 years just by being strategic about how you pay for certain items is one heck of a lifehack.

For us this might mean 5-6 one-way fares for one member of our family and free flights for another. For others it might mean that their significant other flies for free with them. For someone else it may mean being able to take a parent on that trip to see the Grand Canyon that they have been wanting to go on for years.

Will This Work For Everyone?

Now obviously there are people that this strategy is not going to work for – if you don’t fly, Southwest points have little to no value for you. If you primarily travel internationally, other airline cards are going to work much better for you. This is where larger strategies involving transferable membership points (like Chase Ultimate Rewards or American Express Membership Rewards) and fixed-value cards (Capital One Venture Rewards comes to mind). For further reading on the ins and outs of travel hacking, I highly recommend Travel Mile 101’s free Travel Rewards course.

For those that like to keep it simple or those that always say “Oh that sounds too complicated, I couldn’t do it” when presented with the idea of travel hacking I would tell them the following – Just apply for one of the Southwest cards.

If you have a good credit score (690+), no derogatory marks (bankruptcies) on your credit report and normal income, you should get approved easily. Even if you don’t have solid plans on the horizon, as long as you have a Southwest account and some activity every 24 months, your points won’t expire. And don’t worry about your credit score taking a hit, a new inquiry will only reduce your score by 5-20 points – and it will come back up over time as you use the account. If you pay your card off in full every month, you have nothing to lose, and some free flights to gain.

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