How I Earned a Year's Worth of Free Southwest Flights for Me and a Friend (By Only Flying 3 Times)

I should start out by saying that I’m not a huge flyer. I don’t travel for work, I have never earned any “preferred” statuses before, and I generally try to book with affordable airlines like Southwest or Jet Blue.

As someone who tries to keep an eye out for deals, I had heard of Southwest’s Companion Pass before. It’s the ultimate deal – bring a friend with you on any Southwest flight you take, for free! It lasts for the rest of the calendar year in which you earn it, plus all of the following calendar year. You can even use it on flights that you book for yourself using points, essentially getting both you and your friend a free trip.

I should point out that “free” means that Southwest doesn’t charge you for the flight, but you still have to pay a few small security fees, so tickets come out in the $5-$10 range.

In order to qualify for the companion pass, you need to earn 110,000 Southwest points in a single calendar year, or else fly 100 one-way flights. I figured there was no chance I’d ever be flying that much. I only usually flew 2 or 3 trips in a year, and maybe one more set of flights around the holidays. I had only earned about 25,000 points over multiple years of having a Southwest Rapid Rewards account. While it sounded cool, I figured it was out of reach for a budget traveller like me.

Reading The Fine Print in Credit Card Deals

Switching gears for a minute, I’ve always tried to be good about keeping a high credit score. One of the things that boosts your score is having a low “credit utilization” which basically measures how close you come to maxing out your available lines of credit each month. The more lines of credit you have open, and the higher the amounts that they’re for, the lower your utilization will be, which boosts your credit score.

I was talking about this with a friend who mentioned that he had opened lots of different rewards cards for the companies he shopped with the most. While it’s cool to get extra points or cash back by using a merchant’s card at their own store, he told me how lots of cards had great incentives right out of the gate, to get you using their card for all of your purchases. You just sign up, put a certain amount on the card within the first few months and unlock sweet rewards.

That’s when he mentioned the Southwest Credit Card deals. While they usually offer 25,000 points for opening a card, occasionally they have deals where they offer you 50,000 Southwest points if you spend $2,000 in the first 3 months of having the card. The card has an annual fee, but the Southwest rewards points more than make up for it.

They also have two different credit cards for consumers – Visa Plus and Visa Premier, both from Chase – and you can qualify for both cards, essentially earning 100,000 points if you time it right and spend enough to unlock the rewards. If you applied for both in the same calendar year, you’d only need a few thousand more points to reach “Companion” status.

My 5 Month Long Saga to "Companion" Status

I had to admit, I was a little skeptical that this would work. Would Southwest really honor the points? Reading the fine print on the companion pass website, it seemed like it was technically allowed, and there were a few stories on the internet of other people who had earned companion passes by applying for both cards. I decided that worst case scenario I’d earn a few more Southwest points and potentially increase my credit score, so when the 50,000 point offer was made available in June, I applied for their Premier card.

As a freelance software developer, I already need to pay a few thousand dollars to the government every few months in estimated taxes. Fortunately, the IRS works with some payment processing companies that allow you to pay your taxes on a credit card. There’s a small percentage fee that I was charged for paying with a card instead of direct deposit, but I knew the points would be worth it.

Sure enough, 50,000 points showed up in my Southwest Rapid Rewards account a week after I paid my taxes. At the very least, it was already looking like I could get some free flights for my troubles. I just needed the second card to get closer to 110,000 points for the year.

When I went to apply for the second card, they had stopped running the 50,000 points offer, and were only offering 25,000 points. That wouldn’t be enough for me to earn the companion pass, so I had to keep waiting, checking the site every few days to see if the bigger offer was back.

Several months went by and the offer still hadn’t come back up, so I started doing more research. Maybe Southwest had caught onto what people were doing and no longer offered such high offers. I was reading the comments on a blog post that talked about the deals, and a recent comment mentioned how Southwest might have stopped the offer for new card holders, but you could still get 50k points if you’re referred by a current card holder.

The commenter left his email address in the post and said to contact him for more information. When I emailed him, he replied with a bunch of information including a phone number. He told me to call this number, give them my financial information, mention that he had referred me, and then I’d get the other card and the 50k points.

Now obviously, this sounded sketchy. Making financial decisions based on an anonymous internet commenter? Reaching out to him to learn more about a sweet deal? Calling a phone number he provides and giving information over the phone? 🚩🚩🚩 A million red flags were going off, but I was definitely curious. I googled around for the phone number and found it mentioned on a few other threads talking about the Southwest cards. I even called it at one point to listen to the recorded message to see if it sounded legit. When I was transferred to an “agent”, I immediately hung up. Of course, none of this proved anything, how could I verify the number was real?

I tried calling Chase but their phone menu didn’t have an option for “am I about to be scammed or is this legit?” After getting transferred a number of times, and no one seeming to know the number, I figured I’d give up. It wasn’t worth having my identity stolen for some free airline points. As a last-ditch effort, I decided to Tweet the number at Chase to see if their social media team could figure it out.

The fact that they came through – and even mentioned that it was for the Southwest card – lay my fears to rest. I called the number, gave my information and was approved for the card. Apparently the guy who referred me also got 5,000 points. A few days later my card arrived in the mail, I paid more of my income taxes on it, and another 50,000 points showed up in my Southwest account. 🙌 🎉

I still needed a few thousand more points to earn the companion pass. I had tried straight up buying Southwest points earlier in the year, but I didn’t see the part in the fine print where it said those don’t count towards companion pass. Fortunately, I had a few trips I was taking on routes that Southwest flew anyways, so it wasn’t hard to earn the remainder of the points.

The day after I got home from my last flight, I got an email from Southwest confirming my “Companion Pass” status. They asked me to designate who my companion would be – you’re allowed to change it 3 times a year – and then mailed me a card with both of our names on it. Now I have roughly 135,000 Southwest points to book fligts with, and then I simply click a link to add my companion to the flights.

I’ve already booked round-trip holiday flights and a weekend getaway in early December, all for about $20 total in security fees.

Advice for Those Who Want to Try it

It’s important to remember that the points must be earned in a single calendar year so don’t start working towards it in the last few months of the year. Wait until early in a new year to start checking for the 50k offer. This also lets you have the pass for longer, since you get it for the remainder of the current calendar year you earn it in, plus the next full year.

I’d also recommend spacing out your card applications somewhat. If you apply for both cards at the same time, you might find it hard to spend $4,000 across both cards within the first 3 months of having them. Because my 3 months intro windows didn’t overlap, I had no problem spending $2,000 on each of them.

Ideally, you should be putting $2,000 that you would already be spending onto the card. One easy way to do this is by seeing if your landlord will let you pay rent on a credit card. If they won’t, you could also use a service like Rad Pad’s online rent payment system, where they’ll charge your card and then mail your landlord a check.

Finally, if you’ve been waiting patiently for the 50,000 offer to come up and it hasn’t, send me a note and I’ll hook you up with my referral deal.

Good luck, and happy travels!

Edit: Make sure you’re smart about when you apply for the credit cards, so that you can ensure you’ll earn all the points in one calendar year. This reddit thread documents plenty of cases where people messed up and couldn’t qualify.