11 Years with the Southwest Companion Pass… Thousands of Dollars of Free Travel!

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I write about the Southwest Companion Pass quite often since it is by far my favorite perk in the entire travel world. It has saved my family tens of thousands of dollars over the years since I first earned the pass back in 2008! That means I’ve officially had the pass for 11 years. If you are asking yourself “What is the Southwest Companion Pass?”, here is a quick synopsis: The pass allows you to have a friend or family member fly with you for almost FREE an UNLIMITED number of times! I have lost count on exactly how many times I’ve used the pass and exactly how much I have saved, but I can promise you it has been a lot!

Every year, readers and friends are asking me how I have been able to earn the pass all of these years. Of course the easiest way to earn the pass is by applying for the Southwest credit cards (which you can easily do as well!), but that is by no means the only way to earn the pass. Unfortunately earning the pass isn’t as easy as it used to be since many methods are no longer available, but there are still many other ways to earn the pass.

My daughter flying for free thanks to the Southwest Companion Pass

Earning the Pass Every Single Year


2008 was the very first time I earned the pass. I had known about the pass prior, but I was traveling for work every single week and never had a need to actually pay for airfare. If I wanted to fly somewhere else aside from my home city, I could just fly elsewhere on the companies dime as long as the flight price was comparable to my flight home. Towards the middle of 2008 I was still traveling 52 weeks a year for work, Monday through Thursday, but I wasn’t always flying to my client site. Some weeks I was driving and others I found myself flying Southwest. So earning the pass started to be more worthwhile.

At this point you earned credits and not points when flying with Southwest — it was their Rapid Rewards 1.0 program. You needed to earn 100 credits in a rolling 12-month period to earn the pass. During this time I earned credits by flying Southwest, crediting my Hilton “double dipping” to Southwest, and crediting my car rentals to Southwest credits. In late 2008 I earned my first Southwest Companion Pass. At that time the pass was valid for 12 months from when it was earned.

What still works towards earning the passSouthwest flights and car rentals

What no longer works towards earning the passCrediting Hilton stays to Southwest


I had the Companion Pass that was earned in 2008 until the Fall of 2009. I continued to credit my Hilton “double dip” points to Southwest to earn the credits but stopped flying Southwest as much. I was now 100% driving to my project site two hours away, but continued to stay at hotels during the week. I actually went 2 full years without staying at the same hotel two nights in a row and instead checked out and into a new hotel every single night. At one point I was earning 1.5 Southwest credits per stay at Hilton hotels — I vaguely remember there being a 3x point promotion which was huge! So hotel hoping was imperative to earning my Companion pass and maximizing my hotel free nights.

When my Companion Pass expired in the Fall of 2009 I had not earned enough credits to renew it, so I was without the pass for a few months. At that point credits expired 12 months after they were earned and not at the end of the calendar year like they do today. So even though I didn’t renew my pass, I still had the credits in my account accruing to earn the pass.

What no longer works towards earning the passCrediting Hilton stays to Southwest


By Spring of 2010 I had only earned about half the number of credits needed for the Companion Pass. And since credits expired 12 months after they were earned, it was imperative to earn the remaining credits quick. At that time, American Express was still a Southwest partner. I transferred enough American Express Membership Reward points over to Southwest to earn 50 credits, the exact amount I needed to earn the pass. This was a long time ago so I cannot 100% remember exactly how many Membership Reward points were transferred! Those remaining credits then got me the Companion Pass for another 12 months, which meant my pass was set to expire again in Spring 2011.

I assumed this was going to be the last year of earning the companion pass easily. I got married that summer and got a new job which allowed me to stay home a little more! I stayed at the same company, but moved to an internal role. This meant that earning credits towards the pass was not going to be nearly as easy. Although, I knew I’d always be able to transfer American Express Membership Reward points over again if the pass was worth it.

What no longer works towards earning the passAmerican Express and Southwest are no longer partners so you cannot transfer your Membership Reward points to Southwest.


On January 6, 2011, Southwest announced a MAJOR change to their program. They were going to move away from a credits system and to a new points system — calling it Rapid Rewards 2.0. Previously they had a fixed earning and redemption system which was not tied to the price of the ticket. They then moved to a revenue based system. While earning points and redeeming points for a free flight changed drastically, this also meant an entire change to earning the Southwest Companion Pass.

The system moved to the Rapid Rewards program that we know today on March 1, 2011. Anyone who had an active Companion Pass on this date had their pass extended until the end of the calendar year! Since my Companion Pass didn’t expire until April, my pass was extended another 8 months and wasn’t set to expire until December 31, 2011. I felt like I won the lottery as this probably got me another $1,000 in free flying!


In November of 2011 I applied for two Southwest credit cards. At the time, the offer was 50,000 points after meeting the minimum spend requirement. I waited until January 2012 to meet the minimum spend which meant the sign up bonus points did not post until 2012. I quickly spent $10,000 on the card which earned me another 10,000 points towards the pass. This meant I received 50,000 bonus points from the Southwest Plus card, 50,000 bonus points from the Southwest Premier card, and 10,000 points from regular credit card spend (including the minimum spend requirement). This gave me a total of 110,000 qualifying points which is the exact amount required for the Companion Pass. I received the Companion Pass in February 2012. Since my pass expired December 31st of the prior year, I just had one month without having the pass.

What still works towards earning the passBonus points earned from the Southwest sign up offers and regular credit card spend on any of the Southwest credit cards.


Since I earned the Companion Pass in 2012, it was smooth sailing in 2013! The Companion Pass does not expire until the year AFTER the pass is received. So even though I earned it in February 2012, my pass did not expire until December 31, 2013!


I had accumulated a ton of Wyndham Reward points for cheap in 2011 and 2012. I purchased them during the Daily Getaways promotions with the goal in mind to eventually transfer them to Southwest. The cost to purchase these points was ridiculously inexpensive so it was absolutely worth it. I think I paid $650 for about 250,000 Wyndham points

In 2012, Wyndham also offered a promotion where you’d earn 16,000 points after one stay at a participating hotel. You were allowed to earn up to 48,000 bonus points. Wyndham offered this promotion twice during the year. I took advantage of this promotion 5 times and earned about 93,000 points (bonus points + regular points), and an additional 5,400 Southwest points for crediting some stays to miles and not points. I paid around $300 for my 5 “mattress run” stays. At that point, Wyndham also counted no show stays towards points and bonus promotions (that is no longer the case!).

On January 1, 2014, I transferred 336,000 Wyndham Reward points to Southwest which earned me 100,800 Southwest points. All points counted towards the Companion Pass. While I spent about $1,000 to earn those points, I ended up with about $1,600 in value from Southwest (although the value has since changed), plus I was that much closer to earning the Companion Pass once again — I only needed another 9,200 qualifying points. Also in the month of January, I purchased $10,000 worth of Vanilla Reloads at CVS with my Southwest credit card to earn the remaining 10,000 points needed. Again, I was without the pass in January, but earned it pretty quickly in February.

What still works towards earning the passPurchases made on your Southwest credit card (although CVS no longer sells Vanilla Reloads!)

What no longer works towards earning the passTransfers from partner hotels no longer count as qualifying points


Since I earned the Companion Pass in 2014, it did not expire until December 31, 2015. So I did not have to think about it for all of 2015! I love when I earn the pass at the beginning of the year and it allows me almost two full years of having the pass!


I was due with baby #2 in June 2016 and the thought of traveling while pregnant and my 2-year old daughter was not very appealing to me — especially since we were in the thick of the terrible 2’s. Because of this, I was in no rush to earn the Companion Pass and went without it for a few months. Ultimately though, I earned it in the Fall, but actually did not fly Southwest once in all of 2016! Don’t get me wrong though, I did take a few flights that year including my babies first mileage run at 3 months old!

I earned the pass through many methods this year, including:

  • Shopping Airlines shopping portal. I made sure to use the portal for every single online purchase I made. Southwest also had some high payouts in 2016 at some popular merchants, such as Sears and Nordstrom.
  • Credit card referrals. I had the Southwest Plus credit card and gave my referral link to many friends and family members as well as many blog readers (thank you for those that used it!). Southwest caps the number of points you can earn from referrals, so you’ll never be able to earn the Companion Pass solely on getting friends to sign up, but it can definitely help!
  • Rocketmiles hotel. I booked a few hotel stays through the hotel booking site Rocketmiles. Since I wasn’t staying at hotels often enough to earn status, I did not really care about earning the points/stays towards status for these particular reservations. I made sure to credit all my points earned to Southwest.
  • Transferring points from Marriott. I transferred the remaining number of points needed from my Marriott account to my Southwest account. I used to stay at Marriott hotels exclusively when I traveled for work every single week back in 2005 and 2006 so have a TON of Marriott points.

What still works towards earning the passSouthwest Rapid Rewards shopping portal, credit card referrals, and Rocketmiles hotels

What no longer works towards earning the passTransfers from partner hotels no longer count as qualifying points


Since I earned the Companion Pass in the Fall of 2016, I had the pass for all of 2017! However, I wanted to make sure to earn the pass in 2017 so I then had it right away in 2018 without a gap. Fortunately, I was able to spend most of the year earning the points. I was able to earn about 55,000 points on my own by using the Southwest shopping portal, credit card referrals, paying bills via Plastiq (when Chase used to allow you to pay your mortgage through this site), and using my Southwest credit card exclusively on every non-category bonus purchase.

Then in October I applied for another Southwest credit card giving me 60,000 points plus 5,000 points from credit card spend. Since it had been more then 2 years since I applied for the card and I was no longer a card holder, I had no problem being approved and earning the points again. I made sure to hit the minimum spend right away so the points would hit in 2017 and were added to the 55,000 qualifying points I already had. I ultimately earned the pass again in November which meant I had the pass through December 31, 2018.

What still works towards earning the pass: Southwest Credit Card bonus offer, Southwest credit card spend, Southwest Rapid Rewards shopping portal, paying bills through Plastiq

What no longer works towards earning the passPaying your mortgage through Plastiq


Even though I had the pass throughout 2018, I wanted to make sure I earned it again for 2019. It is still my favorite way to save money on travel, so I made sure to make earning the pass a priority. Unfortunately, many methods that I used in the pass were no longer available, so I had to get creative. Fortunately, I was able to earn 50,000 points by referring friends and family members to the Southwest Companion Pass — there was a point in early 2018 where the referral link was actually significantly better than the best available offer, so that helped! I then earned the remaining 60,000 points through credit card spend, paying my mortgage through Plastiq (but that only lasted a few months Chase no longer allowed it), the Rapid Rewards shopping portal, purchasing some Visa gift cards, and one paid Southwest flight. I also volunteered to purchase a few expensive group gifts for friends and then collected cash from them — they thought I was being nice by doing the leg work, but really it allowed me to put a few large purchases on my credit card!

What still works towards earning the passFlying on paid tickets with Southwest, Southwest credit card spend, Southwest Rapid Rewards shopping portal, credit card referrals, paying bills through Plastiq.

What no longer works towards earning the passPaying your mortgage through Plastiq


So here we are in 2019. I still have the pass through the end of the year since I earned it in 2018. I already have a few flights booked using the pass so it is still providing great value to my family. I do find us flying JetBlue a little more due to the non-stop opportunities to the Caribbean, but Southwest is still much less expensive and I do not mind a quick layover in Baltimore (coming from Boston). And having a family member fly free makes a huge difference in the overall cost (or number of points we redeem) for a family trip of 4.

The main problem I am facing right now is that we have made the decision to go for Hyatt Globalist and I will be putting a lot of our credit card spend on my husbands newly approved World of Hyatt Credit Card. That means I will not be earning too many qualifying points through credit card spend with Southwest. I might just see how the next few months go and possibly go the Southwest credit card routes again this Fall. That would then earn me the pass for 2020 and 2021 which means I wouldn’t have to think about earning the pass again for quite some time, which I love! The only problem with this plan is that I need to make sure I am under Chase’s “5/24” rule in the next 9-12 months, which I actually think I will be. Another problem is that there is no way of knowing what the sign up offers will be at that point and if the points earned from the offer will still count towards the pass, but I will keep my fingers crossed! Things always pop up in the deal world, so some other opportunity might present itself as well! But for right now, I do not have an exact set plan.

How have you earned the pass in the past? Will you be earning it this year, and if so, what is your game plan? Comment below!

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. If you presently have 2 RR Chase credit cards with zero balances, can you apply for additional ones with this offer? Also, it looks like it will be easy to earn the 40,000 miles with spending $1000.00 in first 3 months, however, spending the additional $20,000, within the first year ay be problematic and with 2 cards, very difficult as I don’t have that much debt. Thanks.

  2. I ping-pong with my spouse every 2 years. I’m on my 2nd year, so spouse will be getting 2 SWA cards in Oct and we’ll strategically charge in order to get SWA CP by end of 1st week ’20. We use the benefit like crazy!!!

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