Miles & Points 101: Getting Started

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Hi! We're super excited you decided to check out this beginner’s guide to all things miles and points!

Our goal with this guide is to empower you to go from zero frequent flyer miles to your first free flight. 

We hope you’ll invest the time to read through this entire guide because it could change your life (as corny as it sounds). We discovered miles and points at different points over the last ten years, and it completely shifted the course of our lives when we realized we could afford to travel to many of the places we had always dreamed of visiting!

If you make it through this guide (and I hope you will), you’ll spend a lot of time listening to our advice. So, before we dive in, we want to introduce ourselves. 

Meet the authors


Some of you reading this guide may already know me from me and my wife’s YouTube channel, Kara and Nate. We’ve been documenting our travels there for the past 8+ years. We recently completed our mission to visit 100 countries by 2020. Even if you’ve watched all of our YouTube videos, you’ll still learn something new in this introduction because I want to back up to several years before we started our YouTube channel.

Let’s jump all the way back to early 2013. Kara and I had been dating for over six years. I had recently graduated from the MBA program at the University of Tennessee. Kara was graduating in May, and we were getting married in June. 

My contribution to the wedding preparation was planning our honeymoon. Unfortunately, we were both recent college graduates and didn’t have much money to blow on a honeymoon. But like any good soon-to-be husband, I wanted this once-in-a-lifetime opportunity to be really special. So I started poking around the internet to learn how we could make the most of our small budget, and that’s when I first discovered the concept of maximizing credit card miles and points.

Honestly, I was initially skeptical and didn’t dive in immediately. It took me weeks (maybe months) of online research before I finally convinced myself to sign up for my first travel credit card. Unfortunately, when I met the minimum spend and received my points, it was too late to put them to use for our honeymoon. 

Don’t worry, we still had an incredible honeymoon. I found a great deal for a week at a villa on a small private island in Belize (and thankfully, my camera skills have improved over the years).

Shortly after returning from our honeymoon, I started researching how to use the new points I earned by signing up for my first travel credit card. I ended up using the points to book two round trip flights from Nashville, TN to Fort Lauderdale, FL for $12.

I still remember sitting on that flight thinking, “Wow! This is incredible! Everyone around me probably paid hundreds of dollars to be on this flight, and I paid $6.” I remember this moment very vividly. This was the moment I became obsessed with miles and points.

As soon as we got back from the trip, I set out to learn everything I could about earning and redeeming miles and points for crazy cheap flights. During our first two years of marriage (while both working full-time jobs), I tested all kinds of new miles and points strategies, enabling us to visit 13 new countries together.

The more we traveled, the more we wanted to see new places. To put it in the most cliche terms possible, we had been bit hard by the travel bug. Fast forward to January 2015, it was that time of the year when everyone is setting their new year's resolutions, and you have an opportunity to step back and think about what you want from your life, and more specifically, what you want to accomplish in the coming year.

For us, long-term travel was something we had been talking about for the past two years. Then one night in early January over blizzards at Dairy Queen, we had an epiphany. If we really want to travel long term, now’s the time. There is never going to be an easier time than now. Life will continue piling responsibility on top of us; if we don’t do it now, we may never do it.

So that night, we bought a one-way flight to Japan, packed our bags, and left the next day…

Just kidding. We aren’t quite that crazy. But that night, we decided that we would spend the next year saving up and planning a one-year trip around the world. To prove that we were serious about it and to keep ourselves accountable, we started telling all of our friends and family that we were leaving to travel in January 2016. We figured if we told everyone, there would be enough social pressure to keep us from backing out. 

We spent all of 2015 putting the pieces into place to leave for a year of travel. This included putting all of our belongings in storage, moving out of our apartment, selling our cars, saving up every penny possible, quitting our jobs, and most importantly, saving up a ton of FREQUENT FLYER MILES that we would redeem for heavily discounted flights during our year of travel around the world. 

This was when I got REALLY serious about learning everything I could about earning and redeeming miles and points. It became a serious hobby, and we saved up over 1.8 million frequent flyer miles before we left to start traveling full-time.

This might not mean much to you if you aren’t familiar with frequent flyer miles. But 1.8 million frequent flyer miles is worth between $15,000 - $30,000 in free flights!! 

At this point (3 years later), we had earned well over 2 million miles and points and redeemed them for over $25,000 worth of free travel.  [some of them in business]

And we still have points left over that we’ll redeem for more free flights in the future. Okay, that was a long story about me, but hopefully, I’ve built some credibility with you. I hope it’s encouraged you to finish reading this guide so you can start earning deeply discounted flights using the strategies I will teach you in this guide.


Unlike our friend Nate, you’ve probably never heard of me before - unless you’re one of my 213 followers on Instagram (more like 175 if you don’t count my mom and her knitting circle).

My name is Mike, and I’m just a guy who loves to travel. When I say that I love to travel, I mean to say that I’m obsessed with travel. So first, I’ll give you a quick rundown of my story.

I grew up in a small town called Nottingham, New Hampshire. I never really left my hometown until high school and never left the country until after graduating college. My goal in life was to become an opera singer (to this day, I’m not quite sure how that happened), so I spent eight years in college earning three degrees in classical music before starting my career as a freelance opera singer. 

My first two times ever leaving the country were to sing on tour through Chile and in an opera production in Salzburg, Austria, after graduating from college. Immediately after touching down abroad for the first time, my eyes were opened to the many possibilities and experiences I could have by traveling around the world. From that moment, I knew I needed to do whatever it took to make travel a more significant part of my life.

There was one big problem - I was a freelance musician… Not exactly the most lucrative industry to be in to afford rent, let alone a trip abroad. That’s where miles and points came into play.

My first foray into miles and points didn’t come in the form of credit cards, but rather in budget travel. I would spend hours finding the cheapest flights, hostels, and best deals to piece together fantastic trips around the world for meager prices. The next puzzle piece was finding ways to make money while traveling. For Kara and Nate, this was their Youtube channel. For me, it was whatever remote job I could find. 

Once I started to realize how easy it was to work abroad, travel for cheap, and actually make money while traveling, I began to take my traveling to the next level by getting into miles and points.

Within a year, I racked up over 2 million points (using many of the creative strategies outlined in this guide) and traveled on about a dozen flights over a few trips, all for free. 

Hundreds of flights, 60+ countries, and thousands of nights in hotel rooms later, I’m basically a full-time traveler with a steady stream of miles and points that allow me to travel wherever I want, whenever I want. Miles and points have even allowed me to go from budget airlines and hostels to luxury resorts, business class flights, and comfy airport lounges, spending less money than when I started my budget travel journey.

These days I live in beautiful Toronto, Canada, and travel as much as possible. I love everything from exploring the Canadian wilderness in my backyard to exotic and exciting places on continents near and far.

In the past, I’ve mostly kept my miles and points experience to myself. But now, I’m excited that Kara and Nate brought me on board to share them with you through this guide and Daily Drop - our 5x weekly newsletter geared explicitly toward maximizing miles and points to travel for less. 

What exactly is this idea of maximizing miles and points?

For those of you who are just getting started, we’re going to begin simply by answering the question, “What is the concept of maximizing miles and points?” When you start traveling more than usual, your friends will take notice. They’re going to start asking questions. So, here’s a simple way to explain your new travel hobby.

This type of travel simply involves earning and redeeming miles and points for heavily discounted travel.

At its core, it’s actually pretty straightforward.

Step 1: Earn miles and points

Step 2: Redeem miles and points

Step 3: Travel for pennies on the dollar 

When you dive into the details, it gets a little more complicated. Otherwise, you wouldn’t need this guide. But I think many people overcomplicate things, so I wanted to show you that it’s actually really simple.

While learning to travel for less can be much more than just miles and points, this guide will focus on that specific element.

Is using miles and points for you?

At this point, you may be thinking, “I have a full-time job. I can’t just take a year off and travel worldwide. Should I continue reading this guide? Even though I only (insert personal situation), can I still get value from credit card miles and points? Is it right for me?”

Well, I’m glad you asked. There is a common misconception that you must travel a lot to get value out of earning and redeeming miles and points, which is simply not true. No matter your situation, you can probably squeeze out hundreds of dollars of free travel from the strategies in this guide. Let’s look at a few common situations and how each one could gain value. We’ll start with obvious:

The “I want to travel full-time” traveler - I’ve already told you that Kara and I have saved over $25,000 on flights using these strategies. If you’re going to embark on the beautiful journey of long term travel, PLEASE do yourself a favor, read this guide, and take action on what you’ve learned.

The “business” traveler - If you spend a lot of time in the air, this concept can help you maximize the miles you earn by flying. The perks that you can get for free with travel credit cards will make the time you spend in airports and on airplanes much more comfortable. Plus, you might think you’re earning a lot of miles with all of the flying that you’re doing, but later in this guide, I’m going to show you how you can earn way more miles on the ground than you can in the air.

The “one vacation per year” traveler - If you’re like most Americans, you only get a week or two of vacation time. This means you may only be able to take one trip per year. Even if you only take one trip, miles and points can still save you thousands of dollars. How awesome would it be if your one vacation per year was practically free? This is a really likely scenario. If you put these strategies into place, and you focus all your efforts on saving up for one big trip every year, you could pay for it just using miles and points.

The “I have champagne taste but a beer budget” traveler - Maybe you’re in a good financial position, and you can afford all of the travels you have time for. Even if this is you, I bet you still wouldn’t mind traveling a bit nicer. How does a lie-flat business class seat sound on your next 10 hour flight to Europe? Or how does upgrading to the Ritz Carlton instead of the Hilton sound? Even if you can already afford to travel a lot, miles and points will help you upgrade your experience! 

The “I don’t like traveling, but I have to do it once a year” traveler - Even if you hate traveling, these strategies can still help you. Most people end up taking one flight per year for one reason or another, whether it be for business or visiting family for the holidays. The only thing worse than doing something you hate is paying to do something you hate. At least if you use these strategies, you won’t have to pay full price for your next miserable airport experience.

I truly believe that the strategies in this guide can benefit 90% of the people who are reading this sentence. However, before I get you too excited, I have to tell you that there are a few people who are not a good fit for this idea around using miles and points.

Who shouldn’t dabble in the miles and points world

Bad credit score - Signing up for travel credit cards is one of the fastest ways you can earn miles and points. If you have a low credit score, you’re going to need to work on bringing it up before you’re ready to do this. If your credit score is below 700, there’s a good chance you won’t be able to get approved for many of the best travel credit cards. Go work on improving your score, and come back to this guide when you’ve got it above 700.

If you don’t live in the U.S.* - Our YouTube channel has a very international audience (that’s what happens when making videos in 100+ countries), and I’m sure some of you who have made it this far don’t live in the U.S. (although I’ve tried to make it clear that this guide is only for U.S. residents). I wish this guide could be for everyone, but because these strategies rely heavily on signing up for U.S. credit cards (which you can’t get approved for if you’re not a U.S. citizen*), you probably won’t get very much value from this guide if you don’t live in the U.S.*

*Note from Mike: As an American-Canadian, I have to mention that Canadians can participate in the U.S. credit card and points world. In fact, Canadians can even apply for U.S. credit cards using their Canadian credit history! If you don’t want to go down that road, there are plenty of Canadian points programs that these same principles apply to, and even some Canadian-issued credit cards for U.S. hotel and airline programs - so stay with us, Canadians!

Can’t keep spending under control - It would be very irresponsible for me to encourage you to sign up for new credit cards if you can’t keep your spending in check. Please stop for a minute and take a really honest look deep inside yourself. Will signing up for a new credit card tempt you to spend money you don’t have? If so, please close this guide now, and don’t tempt yourself any further. 

If you took the time to read through each of the scenarios above, you probably noticed that each one has something to do with credit cards. Now you’re probably wondering why credit cards play such a vital role in the strategies detailed in the guide.

I know the idea of signing up for credit cards really scares some people. Please keep reading, and don’t give up on this guide. I’m going to explain why credit cards are so important to the process and hopefully tackle the biggest questions you have about signing up for new credit cards to remove any hesitation you may have about moving forward.

So what are miles and points?

Miles and points are basically a form of currency that airlines, hotels, and banks offer in return for loyalty. The first true frequent flyer program was created by American Airlines in 1981 in an attempt to reward their most loyal customers and steal customers away from other airlines. The plan worked, and soon other airlines followed suit. 

Today, loyalty programs can be found almost everywhere you look from your local ice cream shop to the gas station just down the road from your house. As travelers, we’ll focus on maximizing the value of three types of loyalty programs:

  • Frequent flyer miles

  • Hotel points

  • Bank points.

When I say “miles and points,” I’m referring to these three categories as a whole. 

Frequent flyer miles

These are points (aka miles) earned with an airline that can be redeemed for free flights. An example of a frequent flyer program is United Airlines’ MileagePlus Explorer Club. If you are a member of the club (which you can sign-up for online for free) you’ll earn points every time you fly with United. Then, once you’ve earned enough points, you can redeem them for free flights on United Airlines.

One important thing to understand about frequent flyer miles is if you earn miles with a specific airline, you must redeem those miles with that specific airline program. So if you earn miles with United, you must redeem them through United. You cannot earn miles with United and then redeem them for a free flight on American Airlines.

What is also important to understand is that just because you’re redeeming miles through an airline program doesn’t mean you need to redeem them on that airline. I know, I know - that’s super confusing. Let me explain.

Most major airlines belong to a series of “alliances” and also have various “partnerships.” This means that certain airlines team together (usually they all operate in different markets) and let each other book flights on one another’s airlines and even redeem points on their airlines. 

The most prominent examples of airline alliances are Star Alliance, SkyTeam, and OneWorld.

Star Alliance is the largest of these and consists of airlines like United, Lufthansa, Air Canada, Turkish Airlines, and many more.

SkyTeam is primarily focused on Delta, KLM, and Air France but includes airlines like Aeromexico, Korean Air, and more.

Finally, the OneWorld alliance includes American Airlines, British Airways, Qatar Airways, Ibera, and a number of others.

This means that if you have United miles, you could also use those miles to book flights on Air Canada or Lufthansa. The only catch is that you’re booking flights on these airlines through United’s website and loyalty program. This makes the world of points and miles very interesting because you can use U.S. points programs to book travel that never even passes through the U.S. 

A fun example of this is using Delta SkyMiles to book a trip from Amsterdam to Dar Es Salaam, Tanzania on KLM Royal Dutch Airlines. This is an actual booking I made a few years back. I used U.S. points that I earned from a U.S. credit card to book a trip between Europe and Africa. The possibilities are endless, so start memorizing those airline alliances!

A few of the most popular U.S. frequent flyer programs include:

 Hotel points

These are points earned with hotels that you can redeem for free stays.

An example of a hotel points currency is Marriott Bonvoy. If you are a member of their rewards program (which is free to sign up for online), you’ll earn points every time you stay at any one of Marriott’s hotel brands. Once you’ve saved up enough points, you can redeem them for a free stay.

Similar to frequent flyer miles, if you earn points with a specific hotel chain, you must redeem your points through that specific chain. So, if you earn Marriott Bonvoy points, you must redeem those rewards at a Marriott Bonvoy property. The one exception to this rule is the fact that every major hotel loyalty program allows you to transfer points to airlines, typically at a suboptimal rate. We’ll cover that later on.

A few of the most popular hotel programs include:

Bank points

Usually, you earn bank points by signing up for credit cards and spending money on those cards. Depending on which bank you’re earning points with, the points can be redeemed in different ways.

Fixed Value Points - This is less common, but these are points that have a specific value and are generally worth $.01 cent each. As an example, Capital One has an option to pay for any type of travel using their miles as a fixed value of $.01 cent apiece. So if you wanted to redeem these miles for a $500 flight, you’d need 50,000 miles (50,000 x $.01 = $500). Like with Capital One, they can even be redeemed for things like taxi fees and parking - or pretty much anything that could be considered a “travel expense.”

Transferable Points - These are points that can be transferred to different airline and hotel programs. For example, if you were to sign up for the Chase Sapphire Preferred® Card, you would earn Chase Ultimate Reward points. You have the option of redeeming these as fixed value points (as explained above) or you can transfer them to different partners. 

Specifically with Ultimate Reward points, you can transfer them to 11 different airlines and 3 different hotel chains. After you transfer the points, you can redeem them just like you would frequent flyer miles or hotel points that you earned directly with the airline or hotel. Transferable points are great because they offer a ton of flexibility, and you can usually get the maximum amount of value out of transferable points.

A few of the most popular transferable points come from Chase, American Express, Capital One, and Citi.

How most people earn miles & points

Now that you have a better understanding of these mysterious “miles and points,” let's look at a few specific examples of the most common ways people go about earning them.

Frequent flyer miles

All three of the major U.S. airlines’ frequent flyer programs work pretty much the same way. After signing up for their frequent flyer program, you earn points based on how much you pay for the flight. If you have status with the airline, you can earn additional bonus points. But in order to keep this example as easy to understand as possible, we’ll assume that you’re a standard member of the airline’s frequent flyer program.

In my examples, I like to be as specific as possible. So we’ll use United’s MileagePlus again as an example. Below is a chart that tells you how many United miles you’ll earn per dollar spent on a flight based on your membership level. Remember, we’re focusing on the standard member. So in this case, you’d earn 5 miles for every dollar spent (technically, you only earn points for every dollar spent on the “base fare” which doesn’t include the taxes and fees on the airline ticket, but let’s not overcomplicate things at the moment).

Let’s say you book a round-trip flight from New York to Paris for $1,000. You’d earn 5 points for every dollar spent on that flight. So, you’d earn 5,000 United miles for traveling on that flight.

[$1,000 x 5 = 5,000]

Hotel points

You earn hotel points pretty much the same way you earn airline points. You earn a specific amount of points for every dollar that you spend with the hotel. We’ll use the Hilton Honors program as an example. When you’re a part of their loyalty program, you’ll earn 10 points for every dollar spend on your Hilton hotel stay.

Let’s say you book a 5 night stay in a Hilton Hotel in New York City, and your room costs $300 per night. Your total bill would be $1,500. You’d earn 10x points for every dollar spent. So you’d earn 15,000 Hilton points in total for your stay.

[1,500 x 10 = 15,000]

Bank points

The two most common ways to earn bank points are by signing up for a credit card and spending money on that credit card. For example, if you sign up for the Chase Sapphire Preferred card, you’ll earn however many Ultimate Reward points are being currently offered if you spend a certain amount of money in the first 90 days after signing up for the card.

Then, moving forward, you’ll earn 1 point for every dollar you spend on the card. Unless you’re spending money at a restaurant or on travel, then you’ll earn 2 points for every dollar you spend (this is called a category spending bonus).

So let’s say you signed up for the Chase Sapphire Preferred card, and in the first three months you spent $3,000 on the card in order to meet the minimum spend. You spent $1,000 on flights, you spent $500 at restaurants, and you spent the remaining $1,500 on miscellaneous that didn’t fall into the restaurant or travel category. At the end of the three months, you’d have 54,500 Ultimate Reward points.

50,000 point welcome offer + ($1,000 x 2 = 2,000) + ($500 x 2 = 1,000) + 1,500 = 54,500

The fastest way to earn miles and points

Now that you have a better understanding of the most common ways to earn frequent flyer miles and hotel points, I want to illustrate why signing up for credit cards is the fastest way to earn miles and points. If you’ve been skimming through this guide, I don’t want you to miss this important point!

It’s easier to earn miles on the ground than it is in the air!

As backwards as it sounds, it’s actually much faster and easier to earn miles and points by signing up for credit cards than it is to earn them by actually traveling. Let me show you why.

Remember the United Airlines example we used above? In that example, you paid $1,000 for a flight from New York to Paris. As a United MileagePlus member, you earned 5 points for every dollar spent on your flight. This means that your round trip flight to Paris earned you 5,000 United Miles.

Now, let’s look at how easy it is to earn 8x the points just by signing up for one credit card. Chase bank has a credit card called the UnitedSM Explorer Card. When you sign up for this card and reach the minimum spend, you’ll earn a TON of United miles depending on whatever the current bonus is (could be 40k, 60, 80k, etc.). Plus, you’ll earn 1 point for every dollar spent on the card.

As an example, if you were to sign up for the card and spend $5,000 in the first 3 months, in just 90 days you could have 45,000 United miles.

40,000-point welcome offer + ($5,000 x 1) = 45,000

This is a super easy way to earn 45,000 United miles. All you’d need to do is sign up for the card, and start putting all of your everyday spending on this credit card instead of using cash or a debit card.

To earn this same amount of points by flying, you’d have to spend $9,000 on flights with United Airlines. In the example we used above, that would require flying back and forth from New York to Paris 9 times!

Hopefully by now, you’re starting to see why we get so excited about travel credit cards. But before we move on, let’s look at an example in the hotel space.

Remember our Hilton example from above? In this example, you paid $1,500 for a 5-night hotel stay in New York city, and you earned 10 points for every dollar you spent which resulted in 15,000 points.

If you were to apply for the Hilton Honors American Express Card, you could earn another large sum of bonus points, depending on what the current welcome offer is at the time you’re reading this.

For example, let’s use 75,000 bonus points as a possible offer. You could earn those points after spending, say, $3,000 in the first 90 days after getting approved for the card. Plus, you’d earn 3 points for every dollar you spent on the card.

So, if you were to apply for the card and spend $5,000 in the first 3 months, in 90 days you would have 90,000 Hilton Honor points.

75,000 point welcome offer + ($5,000 x 3) = 90,000

In order to earn 90,000 points with Hilton by staying at their hotels, you’d need to spend $9,000 on hotel rooms. Or you could just apply for this credit card offered by American Express.

I think you get the point.

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