I’m a semi-regular Southwest Airlines customer for several reasons.

1. They’re the largest carrier at my home airport of Austin
   
2. My most frequent destination is Washington National airport, and they have the only (legally permissible) non-stop Austin – National
   
3. When I fly with my one year old daughter I usually wind up with an empty middle seat without paying for it

I don’t mind their all-coach product on flights up to 3.5 hours one bit. They offer more more than United, Delta, or American in regular coach. And I can even get an aisle seat when I change flights last minute.

Why I’m Looking Forward to Flying Southwest More in 2020

I’m excited to fly Southwest much more in 2020. That’s because I’ve got the new Southwest Rapid Rewards® Performance Business Credit Card. It’s currently offering 70,000 points after $5000 spend within 3 months (worth about $1050 in airfare by my calculation, and double that with the companion pass). [Offer expired] I plan to earn a Companion Pass at the beginning of 2020 and it’ll be valid through the end of 2021.

That will allow me to take my wife with me on Southwest flights for just the cost of security taxes. Our daughter is still just one year old and flies free as a lap infant.

The Southwest Rapid Rewards® Performance Business Credit Card also comes with a statement credit for TSA PreCheck or Global Entry in the first year. It offers 9000 bonus points each year after cardmember anniversary. It also offers a statement credit for purchasing A1 – A15 boarding four times a year.

The most useful to me though are the inflight wifi credits. The Southwest Rapid Rewards® Performance Business Credit Card rebates Southwest internet purchases up to 365 times per year, including more than once a day. My wife and I, traveling together, are rebated two credits at a time.

Southwest Offers An Elite Status Challenge Over And Over

Southwest Airlines will give you 90 days of status and an expedited challenge to keep that status (3 roundtrips or 6 one ways) if you have status with a competitor airline.

However I learned that when you fly enough to keep the status you don’t get it for the next full membership year, you get it for 12 months. Since my challenge ended September 30, 2018 I kept my status through September 30, 2019. So when I went to check in for my flight on October 4 I had no status – and didn’t realize it – and a C-11 boarding pass.

Fortunately Southwest will let you status match over and over. It isn’t once in a lifetime. You have to wait 12 months between challenges, so you can challenge and meet the challenge, use the status and when it expires you can challenge again. They may not keep those rules, but for now that’s pretty lucrative. The only thing you cannot do is get 90 days of status over and over (without flying the 6 one ways to keep status), since you have to go 12 months between challenges.

I Completed My Most Recent Challenge Too Quickly

I submitted for a new status challenge and was approved. A new wrinkle is that previously booked flights don’t count towards the challenge so since Southwest has no change fees I cancelled my existing itineraries and rebooked them.

There’s a new wrinkle that I hadn’t realized in the challenge, too. When you complete the challenge you get to keep the status for a year. The year runs from the end of the month when you complete the challenge, not from the end of the challenge period.

My challenge, approved in October, would have lasted through mid-January. Had I waited until January to complete the challenge my A-List status would have been good until January 2021. However my Southwest flying completed the challenge in November. As a result my status lasts only through November 2020.

As a result I either need to re-earn my status before the end of November 2020, rather than December 2020, to avoid a gap (of a month) in status or I’ll need to re-submit a status challenge request in December 2020, assuming it’s still being offered.