Travel Strategies: #1, Flights, Credit Cards, and Working The System

We went to Italy on our honeymoon. It was my first experience with international travel. Something about that experience got me hooked.

We went to Italy on our honeymoon. It was my first experience with international travel. Something about that experience got me hooked.

In another life, where I was born about 50 years earlier and the internet wasn’t really a thing and people still needed travel agents, I think I would’ve made a great travel agent. I really love planning trips. There’s something about it that satisfies some penchant in my brain towards orderliness and an organized life. I love sitting down and charting out how long we will be at a place, and what we can see, and making an itinerary to make sure we get to experience everything we want to experience.

But mainly, I’m just one of those weirdos who really likes looking for flights.


One of the incredible blessings of my last 4 or 5 years is that I’ve had the incredible privilege to go a lot of places. My wife and I have had an extended time where we both have pretty flexible schedules, and we’ve taken advantage of that by prioritizing spending money on travel over other things. Neither of us are really “things” people. We would always rather take a trip than buy a new couch. I drove an old car til it died because I didn’t want to have a car payment. We’ve channeled those financial priorities into a lot of travel, and I’ve always thought about writing out some of the tactics that we’ve used to keep that travel cheap. I’ve shared these over the past few years with people as they’ve asked us how we can afford to travel, and I figure I might as well save them for posterity.

Without further ado, here are the 5 strategies I’ve used over the years to make travel as affordable as possible:

  1. Utilize Credit Cards (Wisely)

  2. Pick an Airline, Work The System

  3. Fly To The Coast, Then To Your Destination

  4. Use Google Flights To Compare Options

  5. Destination > Comfort



There is a lot of understandable caution when it comes to credit cards. They can be really, really dangerous when used irresponsibly. If you have a tendency to want to buy things you can’t afford, then completely disregard this first strategy. No amount of travel benefit is worth the risk of serious consumer debt.

With that said, when used responsibly, credit cards are the single biggest aid for us in affording to travel. That’s primarily because credit card companies WANT you to use the card, and so naturally they incentivize you using it. We put all of our spending on credit cards, but we treat them like debit cards. We never carry a balance, never use them to buy something out of reach, but all of our spending goes on our Chase Sapphire card. We put our church giving on a credit card, we pay for our bills with a credit card, we pay for our eating out with a credit card, we book our flights with a credit card.

This way, ALL of our spending is going back to earning us points we can use to make travel cheaper. If you use a credit card responsibly, you reap all the benefits credit card companies put in place to lure in new customers, without any of the consumer debt.

The Credit Card We Use:


I love this card so much. I signed up for it when I got married so I could put wedding expenses on it (and earn those points!), and I’ve used it as my primary spending card ever since. The three best features about the card:

  1. 2x points on Food and Travel

    • Sometimes it feels like this is literally all Erica and I spend our money on. We have the bad habit of eating out too much, but with this card all that money (probably wastefully) spent earns us even more points towards travel. Lots of credit cards throw different points multipliers to incentivize spending, but I feel like this is one of the best. It also feels great to feel like you’re earning points back as you book things for a trip. Spending $400 on a hotel or AirBNB earns you 800 points! It’s a great (or terrible) cycle.

  2. You can use the points on almost any travel partner.

    • Probably the best part about this Chase card is that as you earn points, you can either a) transfer them to another airline like Delta or Southwest or b) book flights directly through the Chase travel portal. This way your points go even farther, because you can use them for domestic flights on US airlines, OR make your international flights cheaper by offsetting the cost with points.

  3. The card is just really nice to hold

    • This is a little less of a novelty now that more credit cards are like this, but the card itself is super heavy and feels really nice. I get comments on it all the time when I hand it over to fast food cash register people as I earn 2x points.

If you decide to sign up for the Chase Sapphire card, will you do it through this link? It gets you a great sign-up bonus and me a bonus as well.



Every airline puts in place incentives to get you to fly with them over other airlines. It absolutely helps you if you pick an airline that you really like, and try your best to primarily fly that airline. You start to better understand how they price their flights, when to look for cheaper flights, how the system works. And then you earn points faster as you fly that airline more. People have a hard time racking up points to use flights if they spread themselves between American, Delta, Southwest, and the like. Sometimes it can be kind of annoying if you need to get somewhere and it’s a little more expensive to fly your airline of choice, but in the long run, it really helps you to zero in on an airline and fly them more than others.

Our Airline of Choice:


The Southwest companion pass is the perfect example of combining strategy #1 and strategy #2. A few years back somebody turned me on to the fact that if you earned 110,000 points in a year, Southwest would give you a companion pass, which means when you fly, a companion flys free. Buy one get one free flights! How could I turn that down!?

There are a million resources out there that will help you understand how to earn it, but long story short: By signing up for a couple of credit cards and earning the sign-up bonuses, you can with relatively small cost (roughly about $300, plus the spending that you should already be responsibly putting on a credit card), earn 110,000 points, plus 2 years of buy one get one free flights. The Southwest companion pass is the single greatest tool I’ve used to travel cheaply, both domestically and internationally. If you can get it, you should. Here’s a link to a good resource that explains the details of earning it:

We almost exclusively fly Southwest, mainly because of the companion pass. With the Companion Pass, our Chase Sapphire Card, and other travel strategies, we hardly ever pay full price for a domestic flights.


I live in Kansas City. There aren’t many great international flights in Kansas City. Inevitably, you’re going to be flying from KC to some other larger city before you take the long trip to another international destination, and then probably one more shorter trip to where you actually want to go.

When you look for flights from Kansas City to an international end point, the flights always feel exorbitantly expensive. Who can ever afford to travel with these prices?

But have you ever looked at international flights out of New York? Los Angeles? They are SO much cheaper. Flying to Asia from LA is exponentially cheaper than flying to Asia from Kansas City. Flying to London from Boston is way cheaper than from Kansas City.

You could take the exact same flight plan, on the exact same airline, but often times, booking the tickets separately can save you a lot of money. A perfect example was when I was looking for flights to Japan. I searched flights on Delta from Kansas City to LA: $250-$300. And then I looked up flights from LA to Tokyo: $750-$800. But when I set the destination as KC-Tokyo? $1500. Same exact flights, same exact dates, almost $500 more expensive.

My strategy for every international flight I’ve ever taken is basically as follows:

  1. Choose my destination.

  2. Find the cheapest flight from a major US coastal city to a major international city. (ex. NYC to London)

  3. Take a budget airline from that city to your destination.

  4. Work backwards and find the cheapest flight to major US coastal city.

In countries other than the US, they almost always have budget airlines where you can get tickets for $50 to $100. It’s WAY cheaper to use those airlines than it is to take a normal US airline (Delta, American, etc.) from your starting point to your ending point. Breaking up the trip into segments will save you SO much money. Makes things more complicated, but it saves you money.

Better to get to your destination in a complicated way than to stay home and wish you could afford a trip, right?

Screen Shot 2019-09-09 at 9.09.25 AM.png



All the credit for turning me on to this strategy goes to my wife, Erica. I was skeptical, but she helped me see how great Google Flights is.

Basically Google Flights is a simple tool that helps you search for flights. It aggregates all the different airlines into one place and compares their prices against one another. I’ve spent hours and hours using this website, and it has helped us save so much money.

You can easily see if it would be cheaper to leave a day earlier or stay a day longer. I can input a departure destination and see the costs to different airports on the specific travel dates I’m looking for. There are a million different ways this can save you money on international flights.

The best way I can show how great Google Flights is is to give an example of how I would use it:


Let’s say I really wanted to take a trip to Rome. I type in “Kansas City - Rome”, and the price it gives me is $1100. Way too expensive for me, I’ll never be able to take that trip.

Enter: Google Flights + these strategies.

  1. I look to see how expensive it would be for me to fly from Kansas City to New York. $173 (or free)

    • If I have the Southwest companion pass, I can fly to NYC or Boston or a coastal destination for free.

  2. I check to see if there are cheaper international destinations to fly into, other than flying directly to Rome. I can see that there is a nonstop flight to London from NYC that is only $361.

  3. I then look up my flight options from London to Rome. I see that there is a flight on EasyJet for $91.

Add those three separate flights together, and you’re only paying $651. That saves you almost $400! If you utilize other credit card strategies, that cost can be even cheaper. In the long run, the flight plan is more complicated. But would you prefer to save money, go on the trip, and have a little more complicated flight plan? Or would you rather say, “Nope, too expensive, I can never go to Rome.”

Pick Rome, every time.

Screen Shot 2019-09-08 at 9.27.27 PM.png
Screen Shot 2019-09-08 at 9.30.55 PM.png
I run almost all my European flights through London. It’s easy to get to from the coast, there’s always cheap flights there, and they have budget flights to everywhere else. It’s always the first place I check.

I run almost all my European flights through London. It’s easy to get to from the coast, there’s always cheap flights there, and they have budget flights to everywhere else. It’s always the first place I check.


I’ve mentioned this a few times throughout, but one of the biggest lessons I’ve learned traveling is that it is worth some travel discomfort for the sake of getting to a destination that you really want to experience. International flights are inherently long, boring, and uncomfortable. Nobody says, “Do you know what I really want to do with my next 24 hours? Sit in an uncomfortable chair for hours, run through airports, navigate lines, and be grumpy”.

But do you know what everybody says?

“I wish I could go to _________”

Sometimes, it requires discomfort to make it to your dream city in a way that you can afford. I’ve got a whole host of terrible travel stories. I can talk about long flights and uncomfortable seats, and weird airports and terrible, rushed meals. But I also have a whole host of great travel stories. And the great travel stories outnumber the terrible travel stories 10>1. There’s never been a travel experience that has rendered the destination we ended up at not worth it. Even the time that I flew from Paris to Ukraine at 3:30am to NYC (JFK) with a bus transfer to La Guardia before a flight back to KC.

It was worth the discomfort, because I got to go to Paris. And Paris was incredible.

Destination > travel comfort, every time.



If all this seems like too much work for you, just sign up for the Scott’s Cheap Flights email newsletter. Wait for an incredible deal to come along, book it, and enjoy all the money you save.

If you have any questions on any of these things, feel free to ask! I’m always up for helping people save money on travel, it’s one of my favorite things ever.

Cory ThomasonComment