How to Fly for FREE in the USA, Mexico, Caribbean, Costa Rica, Belize, Aruba (No Gimmicks!)

Getting a Southwest Companion Pass with Chase Credit Cards

We pursue our Companion Pass by signing up for Chase credit cards. This credit card hack is great for people who pay off their credit cards every month, don’t maintain a balance, and have good credit. All Southwest branded credit cards with Chase have annual fees, and you should consider these fees when determining the total cost of your travel expenses.

In our third year of full-time travel, we flew 50 legs on Southwest. (See this video.) Each leg cost us about $6 in taxes. We estimate the value of these flights, if we’d actually paid for them, was over $4000.

In our fourth year of full-time travel, we flew 10 legs on Southwest. With the exception of the flights to Aruba where extra landing fees are included, we also paid about $6 per segment in taxes. If we would have actually paid for the flights, we would have spent over $2000.

Chase has 5 cards co-branded with Chase. When you sign up for the cards, you can get a sign-up bonus if you spend a certain amount of money in a certain amount of time. If you get two cards around the same time, you will get two sign-up bonuses. Those two sign-up bonuses will generate enough points to get your Companion Pass.

Which Chase Card Should You Get?

With so many Chase branded Southwest Cards, it’s difficult to decide which to pick. You’ll want to read through the benefits of each card to decide which makes sense for you. But you might want to pay a bit more for the Southwest Rapid Rewards Business cards combo because, in return, you get so many extra benefits, which we find very valuable. Here is a chart of the various cards.

To get the Companion Pass, we spend $5000 on the Performance Business card and $3000 on the Premier card which gets us our two sign up bonuses, or 140,000. Plus we get 8000 points from spending the money ($8000), then we only have to spend an additional $2000 to get the extra 2000 points we need to equal 150,000 points in one year.

Name of Card	Annual Fee	Sign up Bonus	Spend/Time
Southwest Rapid Rewards Plus	$69	50,000	$1000/3 months
Southwest Rapid Rewards Plus Priority	$175	50,000	$1000/3 months
Southwest Rapid Rewards Premier	$99	50,000	$1000/3 months
Southwest Rapid Rewards Performance Business	$80	80,000	$5000/3 months
Southwest Rapid Rewards Premier Business	$99	60,000	$3000/3 months

Timing to Get Your Southwest Companion Pass

If you’re going for the Companion Pass, the best time to pursue the pass is in the 4th quarter of any given year. You’ll want to time the moment you get your sign up bonus so that you accumulate all of your required points at the beginning of the year. Thus, your Companion Pass is issued at the beginning of the year and you can then use it for almost two years. 

How to Get a Chase Business Card When You Don’t Have a Business

Even if you don’t technically have a business, you may have a business according to Chase. This quote comes directly from their website, “If your work produces income, you can likely be considered for a business credit card provided you meet that particular card issuer’s qualifications. This could include a minimum credit score or other qualifications. According to Experian, it may be easier to be approved if you have a “good” credit score of higher, Opens overlay—which translates to a FICO^® score of 670 or higher.

Here are just a few examples of businesses or “side hustles” that may be eligible for a business credit card:

• Babysitting
• Dog sitting or dog walking
• Freelance writing
• Ride share services
• Food delivery services
• Tutoring
• Selling vintage clothing online

Here’s how we execute our Companion Pass strategy. Steve and I alternate years so that one year he’s the one getting the cards, then in the third year, I get the cards. We keep the cards for one year and cancel them before the next year’s annual fee comes around.

Thus, in the second year, we don’t have any active Southwest cards. But despite cancelling the cards, the Companion Pass is still good for the second year. In the third year, Chris gets the cards, repeating the cycle.

We start the game in October. In this example, let’s say Steve is the card owner. He applies in the beginning of October and receives the card in late October. He starts spending the required amount of “spend” (the amount of money he must spend to earn the sign up bonus), and he tracks his spend so he doesn’t actually achieve it, saving a few dollars in the balance until January.

Usually Chase gives you 90 days to spend the required amount of money. In the first week of January, Steve finishes spending the requirement amount and gets his first sign up bonus.

In the meantime, in November, Steve applies for the second Southwest card. His second 90 days starts to tick, and he also starts to spend his money. So he’s charging things on both cards, tracking the balances along the way.

As with the first card, he waits until January to finish spending the required amount. By the second week of January, he’ll finish his spend and receive his second sign up bonus. 

When his second sign up bonus hits his Southwest account, he has enough points to get his Companion Pass by the end of January. That Companion Pass will be good for the rest of that year plus the next year, or for about 23 months.

During that time, we’ll fly on all the points Steve accumulated with his sign up bonuses. The points don’t expire, either.

In September and October he cancels both cards to avoid a second year of annual fees. We’ve successfully done this strategy twice per person and have never been denied new cards. Our credit scores remain excellent.

Here’s a chart to help you visualize how this hack works. Please remember, though, that your billing cycles may fall differently, Southwest could change the program, and your mileage may vary! This is the chart that works for us. 

Date	Apply	90 Days	Finish Spend	Sign up Bonus	Companion Pass
October 2024	Performance Card	February 2025	January 2025	January 2025	no
November 2024	Premier Card	March 2025	January 2025	January 2025	yes
September 2025	Cancel Performance Card
October 2025	Cancel Premier Card