(Last Chance?) How To Maximize Southwest’s Amazing New Offer

This post may contain affiliate links; please read our advertiser disclosure for more information.

Southwest Rapid Rewards Performance Business Card

How To Maximize Southwest’s Voucher Cash In System

I have been praising Delta’s handling of the pandemic more than any other airline and program.  From their hassle free cancellation, to their cleaning procedures and blocking of the middle seat, they have done the best in my eyes.  That may have been a little unfair to Southwest because, simply, they pretty much always operate this way.  At least when it comes to their Rapid Rewards program. It is the most consumer friendly program out there that offers steady value, even though never outsized value.  Southwest’s voucher cash in system that was launched today is taking it to a whole another level.  They promised that they would offer members value and boy did they.  So now I wanna show you how you can maximize Southwest’s voucher cash in system.

Update 9/7/20: This may be the last chance to book flights with the intention to turn a voucher into points.  If you have an old voucher with the wrong expiration date on it (9/7/22) you can rebook and cancel now.  Also if you have any Southwest gift cards you would prefer to turn into points today would be the last day.  This is all assuming Southwest does not extend the voucher extensions.  

Covid-19 Voucher Extension Terms

Here are Southwest’s voucher terms, only vouchers that have the September 7, 2022 expiration date will work:

If you decide not to travel, as long as you cancel your flight at least 10 minutes before its scheduled departure, the funds used to pay for a nonrefundable ticket (Wanna Get Away® fares) are normally valid for one year from the date of purchase.

However, in recognition of the current travel environment, we are extending the expiration date of some travel funds:

  • Customers’ funds that have expired or will expire between March 1, 2020 and September 7, 2020, will now expire September 7, 2022.
  • Any travel funds created because you cancel a flight between March 1 – September 7, 2020, will expire September 7, 2022.

For recently cancelled tickets and newly created travel funds, it may take up to five business days for the expiration date to change to September 7, 2022. Typically, the expiration date is updated at midnight after the fund creation.

It’s important to note, while these unused travel funds will be available until September 7, 2022, once the funds are used to make a purchase, the expiration date of the travel funds will then follow our normal ticketing rules and will expire 12 months from the date of purchase.

Should You Cash In Vouchers For Rapid Rewards Points?

Let’s get the first question answered right off the bat, should you turn your vouchers into points? Is water wet?  Does a bear 💩 in the woods? If you didn’t know, the answer to all 3 of those questions is, YES!  The only people that should consider holding their vouchers are people that are chasing status via butt in seat flying. But come on, who is doing that these days?

Here are the reasons you want to take advantage of the voucher cash in system:
  • You are buying Southwest points for 1.28 cents per point going this route. They are usually worth between 1.4-1.6 cents per point when taking taxes and fees into consideration.  You are essentially buying points, with trapped money, at a discount.
  • Rapid Rewards points never expire, vouchers do.
  • Once they are turned into points you can use them on anyone. Vouchers are tied to one person.
  • Rapid Rewards points are more versatile and have better cancellation policies.

Other Ways To Use The Voucher System

Now that we know the value is there how can we take advantage of this new system? I am not talking about the cancellation vouchers you have in your account, because there are some other avenues to consider as well.

Travel & Airline Incidental Credits

If you have some travel and airline incidental credits lying around this could be an option for you. You could buy a Southwest flight, cancel it, and then turn your voucher into points.  This would make your airline incidental / travel credit about 15% more valuable.  There is a risk of devaluation etc. for sure.  Remember that many of these travel credits work on restaurants or grocery stores right now, and that offers less risk.  But if you fly Southwest often and want to get a little extra value out of these credits then this is a option worth considering.

Book Flights With Transferable Currencies For Increased Redemptions

This play is also a little risky, if there is a Southwest devaluation, but if you have an upcoming flight it is a way to get it at a discount.  Let’s say you book the flight through a travel portal using Chase Ultimate Rewards (have to call in) or your Altitude Reserve etc.  You can then cancel the flight, get the better redemption rate and rebook the flight for less points.

An example would be booking a flight for 10,000 Ultimate Rewards points ($150 cost).  After booking, cancel the flight and get a travel voucher.  Turn that $150 voucher into 11,718 Rapid Rewards points.  Book the flight again for 10,000 Rapid Rewards points (assuming a 1.5 cents valuation) and keep the additional 1,718 points in your account.

Purchase Southwest Rapid Rewards Points At A Discount

Let’s say you wanna purchase that same Southwest flight for $150 or 10,000 Rapid Rewards points.  You could buy the ticket for $150 and then cancel it.  Turn the voucher into 11,718 Rapid Rewards points and turn around and re-book it for 10,000 points.  You would be getting $25 in value towards your next flight by going this route, a 16%+ discount on the purchase.


Remember that this all works in theory and is fun to consider.  It takes a day or two for the voucher to update to the proper September 7, 2022 date for the conversion to work.  And these options will only be available until September 7, 2020.

There is also no way to know if the price of the flight will change by the time you can re-book it. Southwest could devalue their Rapid Rewards redemptions as well in the future.  Or they could lock down your account if you abuse it too much.  These are all things to consider before getting too excited about this.  But in small doses it can be a nice win for your travel bookings.

Southwest’s Voucher Cash In System – Final Thoughts

This is an amazing offer from Southwest and there are numerous ways to take advantage of it if you think outside the box a little bit.  I already converted the vouchers that were in my account and started cashing in my airline incidental credits.  I doubt I will take advantage of any of the other plays but it is fun to think about nonetheless. Let me know how you are taking advantage of Southwest’s voucher cash in system in the comments.

Mark Ostermann
Mark Ostermann is a father, husband and miles/points fanatic. He left the corporate world after starting a family in order to be a stay at home dad. Mark is constantly looking at ways to save money and stay within budget while also taking awesome vacations with his family. When he isn't caring for his family or taking a weekend trip, Mark is working towards his goal of visiting every Major League Baseball ballpark.

More Like This


Responses 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. On the Southwest topic, I recently called about the companion pass 6 month extension for those that have it through 12/31/2020. They now hold it through 6/30/21. I was so excited to finally earn mine in January 2020 so I would be able to use it until December 2021, so essentially for a full two years. When I called the rep said that the ones that expired in 2020 did get extended the 6 months. When I explained that I lost the same 6 months he told me that the CEO hasn’t said anything about those expiring in 2021 and didn’t think it would happen. Any thoughts or have you heard anything about this? I’m struggling to understand that those earned before the pandemic won’t get the same treatment when the same travel was lost. Thanks!!

    • I wouldn’t be surprised if they didn’t do anything since most people don’t earn it in the beginning of the year. They are more focused on people that earn it the traditional way towards the end of the year imo.

  2. You mentioned using Airline Incidental credits. Does this mean they’ll include Early Bird Checkin fees in the voucher (and conversion to points)?

  3. I enjoy just about everything this hobby offers but doing anything beyond converting credits to points exactly as offered by SW feels just too over the top for me. Sometimes you have to show appreciation in ways that might not max out your return, but are simply the right thing to do.

    • It depends on how you look at it. All of these options give Southwest cash flow and a much needed interest free loan. So I doubt they would mind.

  4. So if I have a $90 travel credit that expires in Jan 2021, can I book a $100 ticket today for travel on Sept 5 (as an example), cancel it tomorrow, and then after 5 days turn it into RR points?

  5. Just remember that funds DO expire if there’s no activity in 24 months. SW actually states this when you’re waiting on hold to talk to them.

  6. Southwest points “are usually worth between 1.4-1.6 cents per point”. Do you have examples? Most flights I’ve looked at are between 1.2-1.3

    • You are not including the taxes and fees. Look at the cash booking and then look at the points – you will come out at the 1.4-1.6 cents per point amount.

      • Here are some examples (I’ve assumed you earn 4% back on your credit card purchase which is probably too low). Do you have examples of 1.4-1.6?

        BOOK WITH CASH: $75 flight – $3 earned on credit card – 390 miles earned
        BOOK WITH MILES: 4,992 miles needed + $5.60
        EQUATES TO: $(75-3-5.60)/(4,992+390) = 1.23 cpm

        BOOK WITH CASH: $339 flight – $13.56 earned on credit card – 1,974 miles earned
        BOOK WITH MILES: 25,584 miles needed + $5.60
        EQUATES TO: $(339-13.56-5.60)/(25,584+1,974) = 1.16 cpm

        • You are adding in credit card earnings and flight earnings on cash flights which have nothing to do with the value you get when redeeming Rapid Rewards points.

          Should be cash price – $5.60 taxes and fees / rapid rewards points. Your first example is getting you 1.4 cents per rapid rewards point.

          • You are ignoring the opportunity cost of using points which has to be factored in. Any cash flight will always be subsidized by miles earned and credit card points earned. A major theme of your blog is to use credit cards which earn the best return on purchases 🙂

            If I have a voucher for a free shirt at Macys. The shirt is listed at $40 but Macys have a perpetual 25% off coupon. The voucher isn’t worth $40, but at best $30, not including the illiquidity of the voucher

          • We are talking about 2 different things. I am talking about what the points are worth once you have them in your account. That doesn’t change.

            If you wanna calculate whether or not it is worth turning vouchers into points for you then those calculations have weight (including earning points on the flight etc). When determining the value of the points in your account they are not relevant.

          • Re: your Aug 11, 2020 at 7:36 am comment

            The point is that a $100 flight listed on the Southwest website does not cost anyone $100 (unless they are a fool) but more like $85. So when you use points for the “$100” flight you are saving yourself $85. It doesn’t matter if the points are already in your account or not.

          • Fair enough – everyone has their own valuations for points and the way they calculate them. We always encourage you to plug in your own valuations into a calculation.

  7. So how do you make sure the voucher in your travel fund changes to the expiration date of September 7?
    One of my older vouchers still has expiration date of end of this year, and a newer voucher I had was able to convert easily?

    • They should be automatically updated after a day or two (up to 5 per their terms). I would reach out to them and see if they just missed that one.


Please enter your comment!
Please enter your name here


  • MtM recommended tool to track & organize credit cards
  • Best card offers personalized for you
  • Track bonus deadlines, fee dates & 5/24 status
  • Full Travel Freely overview

Free Sign-Up

  • MtM recommended tool to track & organize credit cards
  • Best card offers personalized for you
  • Track bonus deadlines, fee dates & 5/24 status
  • Full Travel Freely overview

Free Sign-Up

Subscribe To Our Newsletter

Join thousands of MtM readers who are subscribed to receive a once daily email with all of our posts. Never miss out!

You have Successfully Subscribed!