Don't miss out! Join the thousands of people who subscribe to our once-daily email or our free miles and points Facebook group with all the best travel news. Points With a Crew has partnered with CardRatings for our coverage of credit card products. Points With a Crew and CardRatings may receive a commission from card issuers.

Now is the time to lay the groundwork to get Southwest flights Buy One, Get One flights for all of 2020 and 2021.  My family first started taking advantage of the Southwest Companion pass at the beginning of 2014 when I earned it for 2014-2015.  Next, my wife attained it for 2016-2017.  Once her Companion Pass expired, I got it again for 2018-2019.  We are at the end of my second run and it is time for my wife to pick up the torch again.  The process to earn the Companion Pass is not as easy as it was before last year.  Both times I was able to hit the threshold by signing up for two personal cards, each with a 60k welcome bonus on the same day.  Unfortunately, this strategy no longer works.  However, even with the increased difficulty the Companion Pass remains one of the best travel perks out there and Southwest continues to be a great airline for families as well.

What is the Companion Pass?

The Companion Pass is a perk that allows you to book BOGO flights with a travel partner for two calendar years. Once you earn the pass, you can book a flight with points (plus taxes and fees starting at $5.60 each way) and then add your companion at no charge besides the taxes and fees.  The companion pass can be achieved by earning 110,000 Rapid Rewards points in a calendar year.  Check out this post from Dan to learn more about the CP!

How Do I Earn the Companion Pass?

You can earn the required 110,000 Rapid Rewards points through flying Southwest, making eligible purchases on a Southwest credit card or my favorite method…welcome bonuses.  While the days of applying for two personal Southwest credit cards to hit the threshold are a thing of the past, the perk is still well within reach.  Nowadays, the simplest way to earn the Companion Pass is to sign up for a business and personal card at the same time.

What Cards Can Help Me Get There?

Currently Chase offers a total of five Southwest Rapid Rewards Credit cards.  While all of the cards have varying levels of benefits and for many flyers make sense to keep long term, I will focus on the Rapid Rewards points available through welcome bonuses to help us reach the Companion Pass.

Each offers the ability to earn 40,000 points after you spend $1,000 on purchases in the first 3 months of account opening.  Plus, they provide the option to earn an additional 20,000 points after spending $12,000 on purchases in the first 12 months of account opening.

There are two business card options as well

How I Plan to Earn the CP this Round

Our strategy will net 120,000 Rapid Rewards points through two welcome bonuses.  We will sign up for the Southwest Rapid Rewards Plus Credit card with a $69 annual fee and the Southwest Rapid Rewards Performance Business with a $199 annual fee (Check out Dan’s review of the business card here.).  I am choosing the Plus as the personal card since it has the lowest annual fee and the Performance Business card has all the perks that I would get from either higher end personal card.  I understand this approach will be tough for many readers with the 5/24 rule.  Others may not be sure they have a business that would qualify, but this article may help.  If you can qualify for both cards, then we are entering the sweet spot to position yourself for 2020-2021 BOGO flying!

Why Now the Best Time to Start Working Towards the 2020-2021 Companion Pass

Since your companion will be able to fly for free on any of your bookings in the year that you earn the Companion Pass AND the following calendar year, you want to maximize the time that you have the benefit in the first year.  The best way to do this is to earn the Companion Pass as early as you can in the new year.  Since it generally takes time (for most of us) to hit the spending requirements for the bonuses, it pays to start working towards those now.  Chase gives three months from sign up to reach the spending requirement necessary to earn the welcome bonus.  Typically, it is ideal to apply in the second or third week of October which would give until mid-January to hit the spend requirement.

Be Mindful of Your Spend!

The key…and I cannot stress this enough, is to make sure you don’t reach the spending requirement and activate the bonus before 2020.  It would be a shame to do all the planning and then mistakenly eclipse the threshold in December.  This would be effectively mean throwing away a year of BOGO flights.  The best approach is to get within $100 of the spending requirements and then wait until the beginning of January to make the purchase that pushes you over the spending requirement to trigger the bonus.  Also, make sure the purchase has enough time to post before the statement closing date.  That is why it pays to have a buffer into mid-January.  Once the January statement closes, it will be a few days until the points are credited and you can enjoy nearly 24 months of BOGO Southwest flights!

Conclusion

With the expanding number of Southwest flight options, particularly to Hawaii, Mexico, Central America and the Caribbean, this perk can provide a ton of value.  The fact that you can earn this for two years from a fairly low spend and a little preparation makes it an even sweeter deal.  I am planning on extending our run with the Southwest Companion pass and hope you can earn it too!

Have you earned the Southwest Companion Pass, or do you plan to?  Did you accidentally hit your spend too early? Tell us about it in the comments!


Points With a Crew has partnered with CardRatings for our coverage of credit card products. Points With a Crew and CardRatings may receive a commission from card issuers. Other links on this page may also pay me a commission - as always, thanks for your support if you use them

BoardingArea

Sign up for our once-daily email with the latest tips and tricks on how to travel for free / cheap. 

You have Successfully Subscribed!