Airline Travel Hacking for the Busy Professional

I recently read an article by DocG titled Inefficiency and Luxury in which he stated that he has never tried to get any frequent flyer rewards, and in fact doesn’t even have a frequent flyer number. This statement left me a bit confused when I first read it. I’m not one who likes to leave money lying on the table. Then he said this, and it all became clear:

“I utterly hate keeping track of frequent flier miles, tracking numbers, or dealing with rotating credit cards. Spending my time doing that will actually cause me to have a decrease in level of happiness.”

I realized that I would also be unhappy spending time doing those things. Yet I have been getting free flights for years and never did any of that. I realized that busy people want efficiency, so I thought I would share how I get free flights the easy way, without the hassle DocG was conveying. Here is how to travel hack flights the easy way.

I started using a frequent flier program after my residency. One key is to be a loyal customer to just one airline. We live in a small town, at the time we started accumulating frequent flyer miles there were only two airlines flying in and out of our nearest airport. I chose the biggest airline, which was United Airlines and started my travel hacking decades before travel hacking was a thing.

When you primarily fly on one airline, all the flights get concentrated in one rewards system. Every now and then I need to fly on a different airline for convenience sake, so I miss out on getting rewards points for those flights. Tracking multiple rewards programs would be a hassle for me so I just use one.

To increase my frequent flier miles even faster we got a credit card that accumulated frequent flier miles for United with each purchase. We started using this card for all our purchases. Having all our purchases on one card also made tracking our expenses easy, as almost everything I spent was listed in the monthly credit card bill.

With the acquisition and management of our 64 rental units, we began using this same card for all the purchases needed for our rentals. Every carpet, stove, refrigerator and dishwasher went on the card. I paid all my contractors with that card; electricians, plumbers and painters.

With all my expenses on one card, not only was my financial life more convenient, but I was racking up a ton of frequent flyer miles. One mile for every dollar spent. We were spending more than $120,000 a year on that card.

I book my travel online. When I need to fly somewhere on business, I pay for those tickets with my frequent flyer credit card and get reimbursed for those deductible miles. Then I get frequent flyer miles for the distance of the flight and miles for charging it on my card. I reserve the free flying for personal trips, ones that are not deductible.

When it is time to book a flight for a personal trip, I log onto the United website and look at their flights first. I almost always can book with them. One round trip in the continental United States usually requires 25,000 frequent flyer miles. Sometimes they are on sale for 20,000 miles.

I simply click on the flight and print my ticket. Lately, the ticket just shows up on my United App.

While I was managing my rentals, I was accumulating approximately five free flights each year without any hassle.

There was a period when my kids said they didn’t want to go on anymore vacations, they wanted to stay home and play with their friends. So, we cut way back on traveling during that period. My frequent flyer account grew to over 800,000 points. That is 32 free flights accumulated with no effort.

When the boys were both in college, my wife and I began traveling again. I have rarely paid for an Airline ticket in the last nine years.

The United website has become very user friendly. I can now see all the flights at once and decide which days have the cheapest tickets. Sometimes I have to pay 50,000 points for a ticket if the 25,000 point option is already sold out. Paying double when the price is zero is still a free flight. There are no blackout days to contend with at the 50,000 point price. It is only the 25,000 point flights that have limited availability. So if I book early, which I usually do, I almost always have the 25,000 point option available.

It is important to note that the best deal is traveling in the continental United States. When you switch to overseas, the number of points you need doubles. But remember, doubling $0 is still $0. I used frequent flyer miles for our recent flight to Europe to walk the 450 mile Camino de Santiago. That saved me a couple thousand dollars.

To sum up Airline Travel Hacking for the Busy Professional:

1: Choose only one airline that serves your airport with the best flight options.

2: Get their rewards card and use it for everything you buy. (Remember to always pay it off every month since paying interest would negate all the value of the free flight.)

3: Use points first for every flight you take, when it is convenient to do so.

I hope that is simple enough for even the busiest professional. I don’t like to leave free money on the table if I can pick it up with minimal effort. I think this is very minimal effort. To save even more time you can pay a travel agent to book the flights for you. Just give them access to your rewards account and they will do all the work and create even less effort on your part. I think it only costs about $25 for them to do the work.

Bon Voyage.

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6 thoughts on “Airline Travel Hacking for the Busy Professional”

  1. Cory, why don’t you just get a couple of the best cash back cards out there? That way you get cold hard cash that you can spend on anything, including travel. No hassle and you are not at the airlines mercy.

    • Kieran, Yes you could do that. But when I calculated things, I got more value from the airline giving me a ticket, than getting cash back and buying a ticket. The cash back is only cash and is a fixed amount, but the airline ticket might be much more expensive. Also the cash back doesn’t take advantage of teaming up with the actual miles from the airlines. Thus I don’t use the miles if the ticket is cheap, like $79 to fly to Vegas is not worth using miles. I buy the $800 ticket with miles. I will also still need to buy the airline ticket anyway so the cash back didn’t save me anything and provided less value. So I haven’t switched to cash back. My son, who rarely flys, uses a cashback card and that is better for him. If you fly alot, I think you might get a better value. I’ve never felt at the airlines mercy or that I had to go through a hassle to get the ticket. Buying with miles is no more a hassle than buying on expedia.

  2. I like this method of travel hacking much more than the churning through credit cards that other bloggers have mentioned.

    Although there will be a lot of points left on the table by not churning credit cards, like DocG I am at that stage where I prefer convenience and not work for something meant to be enjoyable like a personal vacation.

  3. Thanks 4 the heads up! Happy u r enjoying life! I also want to walk the Camino. Missed ur share for that adventure. Got any wise words? Would love to hear about it! Roxanne McCoy.


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