How to fly for free is probably not a topic you would be expecting from me. I have had one post before about travel, but I like to stick to mostly financial topics. However, to me this is a financial topic. I love to travel. However, I also love being as frugal as I can be. What’s more frugal than flying for free? I want to be able to travel and enjoy some things in life, but also stick to my written financial plan and stick to my goal of becoming financially independent by the time I’m 52. Flying for free is a way I can do both. Let me tell you how

Just got this email a few days ago…Oh yeah

What is Southwest’s Companion Pass?

I’m sure there aren’t a lot of people who don’t know what this is by now, but just in case let me explain. If you earn a companion pass from Southwest, that means any flight you book you can bring a companion for free (there is a $5.60 governmental fee each way). That means any flight I book whether it be by paying money or using points, I can bring someone with me for free.

There is one limitation. You have to name one companion. You can change the named companion up to three times a year. But you can only bring the named companion.

One amazing thing is that you get the companion pass for remainder of the year you earn it in as well as the entire next year. Since I earned it in February 2020, I get to have it for the rest of 2020 as well as all of 2021. Pretty sweet right?

How to Fly for Free by Earning Companion Pass

There are a couple different ways to earn the companion pass:

1) Fly 100 qualifying one way flights in a calendar year:

That is a lot of flights for a dentist. For some people who travel for work, that may be possible. But I have a dental practice and I need to be home for my patients. More power to you if you can earn it this way, but I couldn’t. So how did I earn it?…

2) Earn 125,000 qualifying rapid rewards points in a calendar year:

The easiest way to do this is with credit cards. With Southwest credit cards from Chase you usually get a pretty good sign up bonus. Make sure you know all of the rules before you apply to make sure you qualify for the bonus. I have seen bonuses anywhere from 40,000-75,000 points. Every dollar you spend on the card you get 1 point. So if you get a 40,000 point bonus, you will need to spend $85,000 on the card to reach the 125,000 point level. That is a lot of money. But for those of you with a dental practice, that should be doable with all of your business expenses.

But wait, there’s more. You can get two credit cards and two bonuses that both count towards the 125,000 points. It has to be one personal card and one business card. This is how I did it. I got a 50,000 point bonus personal card, and a 75,000 point bonus business credit card. All I had to do was meet the minimum spend requirements for the bonuses and voila, I had over 125,000 points.

So currently I have 133,000 rapid rewards points and a companion pass. I can use those 133,000 points to book my next several flights for free, and then bring my wife with me for free with my companion pass. It’s really a smoking deal.

Why would a Dentist want such Freebies?

Dentists and doctors are too good for free flights with Southwest right? We need to fly first class with caviar. Wrong. Look, I don’t want to save every penny I ever earn and never enjoy life just to reach financial independence. But I also don’t want to be stupid with my money. I am definitely not too good for Southwest, especially when it’s free. I don’t know about you, but even when I’m a multi millionaire I will be getting a Southwest Companion Pass and using it.

I’m also fine with Toyotas, public school, and steak from Texas Roadhouse. It is this mentality I believe that will help me reach financial independence and have the choice about how much I want to work at an age where I can still enjoy life and travel the world.

Disadvatages of Flying for free with the Companion Pass

To me there are none. But I suppose having to fly Southwest isn’t ok for some. You don’t get a seat assignment and there is not first or business class. Oh well. You do get free bags and you can change or cancel your flight at any time without a fee. It sounds like the disadvantage section is turning into another advantage section.

Southwest also doesn’t fly to a lot of places out of the country. However they did just add flights to Hawaii and yes, Companion Pass works for going to Hawaii too. I still like to go to Europe and other places as well. There are two ways I pay for this. First , with the money I save by flying for free with Southwest to most places, I can save and use for flights on other airlines to other places. Secondly, I play the credit card game outside of Southwest too. See this post for more. I have got free flights on several airlines with several different credit cards.


I just earned Southwest’s Companion Pass for the rest of 2020 and all of 2021. With that I have 133,000 points which will be good for at least 5-6 round trip tickets for me. Plus, every flight I am on whether I booked with points or money, I can bring someone with me for free. It really is an amazing deal.

I don’t feel like I am too good for Southwest. I also look for deals on food, shoes, clothes and more. Trust me I don’t live poorly. I am very blessed. But I do look for ways to maximize my dollars. I believe this mentality will help me reach my financial goals.

Look into travel hacking and ways to travel for cheap or free. I have earned a lot of free flights and hotel stays and plan on continuing to do so. I love to travel, but I’m not going to let it force me to have to work until I’m 70. We can travel well and still reach FI and at early age. It just takes some research and game playing. But hey, it’s fun for me.

-Debt Free DDS

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*Nothing on my website is professional or legal advice. I am only sharing information that I have learned and it may or may not be accurate. I am not liable for any problems you may have by following this advice. Please do further research and get professional and/or legal advice about any of these topics. This post likely contains affiliate links. This site could be paid for clicks or purchases made through these links. See my disclosure here.

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