The Best Deal in Travel Is the Southwest Companion Pass and It’s Not Even Close. [Oct/Nov Is the Best Time to Apply for 2 Chase Credit Cards to Get It]

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Every time you buy a Southwest flight with money or points, your partner will fly with you for free for nearly 2 years… that’s the best deal in travel.  And it’s called the Southwest Companion Pass2-for-1 airline tickets are an outrageously amazing deal. 

The key is to earn the currently awesome sign-up bonus on the Southwest Rapid Rewards® Premier Business Credit Card.  BUT, there are other quick ways that I’ll show you in a moment.

Keith on our team says he’s saved at least $5,000 using his Southwest Companion Pass.  Our co-founder Emily also loves using her Southwest Companion Pass.

So that’s one level.  But here’s where it gets absolutely crazy: 

  • Southwest doesn’t do “blackout dates.”
  • Southwest gives every passenger 2 free checked bags.
  • Southwest has the best cancelation policy in the business.
  • Southwest is a transfer partner of Chase Ultimate Rewards points. 

So that means you can easily move points from your Chase Sapphire Preferred® Card, Chase Sapphire Reserve®, and Ink Business Preferred℠ Credit Card to Southwest.  Usually 50,000 Chase Ultimate Rewards points (the sign-up bonus for the Chase Sapphire Preferred after meeting minimum spending) are worth ~$750 of Southwest flights.  But with the Companion Pass… you’re obviously DOUBLING that to $1,500 because your partner flies free with you — for up to TWO YEARS.

Don’t Turn Your Nose Up at Southwest Airlines.  They’re Consistently Rated as a Top US Airline for Good Reason!  And Southwest Flies All Over America, the Caribbean, Mexico, and Central America!

We keep waiting for Southwest to pull the plug on this ongoing deal, but it’s been going strong for many years.  If you want to fly often with your partner, this is the deal to get.  And October/November is the ideal time to go for it because of how the deal works.

What you want to do is earn 110,000 qualifying Southwest points in a calendar year.  Calendar year.  That’s the key.

In short, get the 2 credit cards and meet your minimum spending requirements at the very end of December (not before) so you get all your Southwest bonus points at the start of 2019.  That way your Southwest Companion Pass will be valid for 2019 AND 2020.  Hot dog, that’s incredible.

Here’s How to Earn the Southwest Companion Pass

Get 2 Southwest credit cards (1 personal and 1 business card).  Chase doesn’t allow you to have 2 “personal” Southwest credit cards.  As for the small business credit card, you’re eligible if you’re running a for-profit side-hustle or a more established business.  Chase wants you to grow your business with their cards.

I’ve been approved for Chase business credit cards using my social security number (no tax ID needed) for my sole proprietorship.  Keith and Jasmin on our team have been approved their businesses re-selling products on sites like eBay.  And Meghan on our team has been approved for her small business renting out vacation properties.  I’ve recommended Chase business cards to my friends who are private practice doctors, restaurant franchise owners, real estate agents, and tutors.

But if you don’t have a business, I’ll show you other ways to earn the points for the Southwest Companion Pass in the next little section.  And you can decide if that works for you.

The easiest way is to get yourself the Southwest Rapid Rewards® Premier Business Credit Card and the Southwest Rapid Rewards® Plus Credit Card.  Some folks (including our team members) report being approved for both cards on the same day.  And the general rule of thumb is you won’t be approved for more than 1 personal and 1 business Chase card every 90 days.

3 Easy Ways to Earn the Remaining Qualifying Southwest Companion Points You’ll Need

1. We really appreciate it when you use our links to apply for credit cards because it pays our bills so we can write more and more travel tips and in-depth how-to Guides for you!  But… once you have a Southwest personal credit card, Chase will ask you to refer your friends and family to sign-up for the card you have.  And whenever someone signs-up through your link you’ll earn 10,000 points up to a maximum of 50,000 points per year!

2. This one is super simple.  Book your hotels on  It’s worth it to get your Southwest Companion Pass!

3. Shop.  Southwest has a travel site called the Rapid Rewards Shopping Portal.  Oftentimes they run great deals where you can earn hundreds or thousands of points that count towards your Companion Pass!

The Southwest Companion Pass is game changer.  Suddenly the US, Caribbean, Mexico, and Central America are all within reach… two-for-one airline tickets and free checked luggage.  And you’ve got a constant steam of new travel points coming in from your Chase Sapphire Preferred® Card, if you want.  It’s so cheap to fly this way, you’ll be tempted to jet off for a weekend whenever you want!

Million Mile Secrets features a team of points and miles experts who have traveled to over 80 countries and have used 60+ credit cards responsibly to accumulate loyalty points and travel the world on the cheap! The Million Mile Secrets team has been featured on The Points Guy, TIME, Yahoo Finance and many other leading points & miles media outlets.

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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