Money at 30: Our Latest Credit Card Point Redemption Win

In the past few years, I’ve often written about earning credit card rewards and maximizing my setup to get even more of them. Yet, my plan for redeeming all of these points has been less thought-out. In fact, aside from buying a backpack and a hotel stay (that I later had to cancel), we haven’t really tapped points from our Chase or American Express cards. That was until today, when I realized we could actually save money by paying for a flight with points instead of cash — making a last-minute trip booking a win.

Our Credit Card Point Redemption: A Chase to Southwest Transfer

Searching for fares

Long story short, my wife decided to book a trip for this upcoming weekend. Unfortunately, as you might expect, a lot of the options we were looking at were proving pricey. However, I then had the idea that we could check in with Southwest. Although the airline doesn’t fly to Springfield, I figured it might be worth it to drive to a close-enough city and have her fly from there.

Sure enough, we found some flights departing from St. Louis that would fit her schedule. Even better, the direct flight showed a round-trip fare of about $400 — which was 50% lower than some other options we were looking at. However, before booking, I had an idea: check the price with points.

To their credit, Southwest’s site allows you to search point fares without having to log in. In contrast, I’ve encountered other airline platforms that won’t even let you view these fares unless you have enough points to cover them. Anyway, after running a search and selecting the same flights she was looking at, I realized she could book the flight for about 28,600 Rapid Reward points as well as $11.20 in fees.

Since Chase points can be transferred to Southwest at a rate of 1:1, I figured we’d essentially be spending around $300 in points for a $400 round-trip. So, after deciding that made sense for us, it was off the make the transfer.

Transferring from Chase Ultimate Rewards to Southwest Rapid Rewards

Because Southwest doesn’t serve our local airport, my wife didn’t actually have an account with the airline. Luckily, opening a Rapid Rewards account was fairly simple and only took a couple of minutes. After that, she was able to head to her Chase account and link it to her new Rapid Rewards.

As I anticipated, Chase only allows you to transfer points in denominations of 1,000. So, since her flights required just over 28,600 points, she need to transfer a total of 29,000. Conveniently, the points arrived in her Rapid Rewards account nearly as soon as she hit the button. With that, she was all set to book.

Booking the flight

Finishing up our redemption was super straightforward and simple — at least for anyone who’s booked a flight before. Since there were fees of $11.20, she needed to enter a credit card number in addition to selecting to use her points. Funny enough, we elected to put the charge on our American Express Platinum card to get that 5X point (on $11, that’s a whole 55 points!). After a couple more clicks, the deed was done.

Was it a good value?

Depending on who you ask, we either did well or short-changed ourselves. I definitely lean toward to former opinion — which is why we did it. As I stated earlier, to me, spending $300 in points for a $400 flight sounds like a great discount. Furthermore, had we used the Chase Ultimate Rewards travel portal to book (note: Southwest flights aren’t featured on said platform), the 1.25¢ per point rate we’d get still wouldn’t be as good as this nearly 1.38¢ per point. Thus, win!

However, if you look at The Points Guy, they estimate that Southwest points are worth 1.5¢ each. Therefore, they argue we could have “saved” $30 but paying in cash. That’s fair enough… but it also feels a bit like the perfect getting in the way of the good. Therefore, if I had to do it again, I’d stick with our ultimate choice.

Seeing as we’re still pretty flush with points after getting our Chase Sapphire Preferred card last year, it was high time we redeemed some of our earned rewards. The result is not only a “free” flight for my wife but a higher value for our points than if we’d just taken them for cashback. With all that considered, I’d say this was a big win — and makes me excited to explore future, larger redemptions.


Kyle Burbank

Kyle is a freelance writer and author whose first book, "The E-Ticket Life" is now available on Amazon. In addition to his weekly "Money at 30" column on Dyer News, he is also the editorial director and a writer for the Disney fan site and has recently starting publsihing his own personal finance blog at

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