Christmas In February? The #1 Reason I Love Booking Flights With Southwest Airlines

There’s A LOT to be said for an airline that goes against the grain of oppressive traditional air travel and offers better perks than its competitors. Or perhaps, words aren’t necessary when you are voted “2019 Program of the Year”, “2019 Best Customer Service”, and “2019 Best Redemption Availability” by frequent fliers around the world.

Two free checked bags, no cancellation penalties, free flight changes…what’s not to love?

Ok…Ok…their boarding process could use some work but let’s save that for a different blog.


Prior to 2019, I hadn’t flown Southwest with any frequency. Typically, I chose flights where I would accrue miles that could be used for future international travel (e.g. Delta, American, United).

However, during the past year I’ve found myself on more domestic Southwest flights than any other airline.

I had no intention of Southwest becoming my “go-to airline” but with an infant daughter that requires a stroller, a car seat, diapers, sippy cups, and many backup outfits, complimentary checked bags with Southwest simplifies flying for me.

As the race to eliminate perks and pay for everything continues across all airlines, I have found myself swayed by the simplicity of Southwest. 


Personally, when it comes to buying a flight, 90% of my decision is dictated by the price. Similar to most people, the cheaper, the better. However, if you have to change any details of a flight (e.g. departure time, dates, etc.), it’s a pain!

Typically, airlines will charge a “change fee” and then charge the “difference in fare.” Depending on when you bought the ticket, the changes could cost more than original ticket.


Plans change! You shouldn’t be penalized for things that are, potentially, out of your control and Southwest understands that. Southwest doesn’t penalize a customer for wanting to alter departure time or cancel a flight altogether. In a customer-friendly move, the carrier makes changing a flight so easy, a caveman can do it (remember that commercial? …bum bum pssshhh).


But did you know that you can save money by rebooking the same flight if the price drops? It’s true! Rebooking requires minimum work and can reduce the overall cost of your flight significantly.

I like simplification so here’s an example… 


Southwest offer sales frequently so there is a very good chance the price of your ticket may have changed. If you find out that the price has dropped, sign in to your Rapid Rewards account…

Click on “My Account”…

And click on either “Change flight” or “Cancel flight.” From there a list of new flight options will display the difference between your current reservation and the new one you’re about to make.

Currently on my SWA profile: My upcoming flight to Las Vegas

At that point, if you see a cheaper flight, you simply select the flight that you want and confirm your choice. Additionally, the number of changes is unlimited.


Again, Southwest has gone against the grain and not partnered with third-party travel sites. With this model, Southwest flights do not appear on travel search engines, such as Google Flights, Orbitz, Hopper, etc. You have to go to the Southwest website/app and search for your specific flight date for the lowest price.

Once I book a Southwest flight, my strategy is to check once a week to determine if the cost of my flight has decreased.

Although it’s a little bit of a hassle and sometimes doesn’t pan out, when it works, IT REALLY WORKS!


There are two circumstances here:

  1. You booked the flight with a credit/debit card (we talk about credit cards on this site A LOT. Hopefully, you didn’t use a debit card) 😉
  2. You booked the original flight with Rapid Reward Points

If you booked your flight on a credit/debit card, then the remaining balance is refunded in the form of credit in your Southwest Rapid Rewards account. You have a year to apply the credit toward another reservation or it’ll expire. The best strategy is to look for another Southwest sale, and apply it then.

However, if you redeemed Rapid Rewards Points for your flight, then the difference in points will simply be refunded to your account with no time restriction.

IMPORTANT NOTE: Southwest uses a revenue-based award chart, which means that if the cash price decreases, then the price in points drops too.

Rapid Rewards points don’t expire so long as there’s activity on your account at least once per 24 months. If you have the option, using points offers even more flexibility in case you have to make new travel plans with Southwest Airlines.


A few weeks ago, I booked a roundtrip Southwest flight from Atlanta (ATL) to Washington D.C. (DCA) that takes place this month. The cash prices were a bit expensive so I paid a total of 18,140 points + 11.20 in taxes for non-stop flights (9,070 points + $5.60 each way) and was satisfied with my choice.

This morning I received an email from Southwest that says “We are having a sale and flights start at $49 ($39 for inter-island Hawaii).”

Here is the DIRECT LINK if you’re interested.

I took a look at the price calendar for flights between Atlanta and Washington D.C. and see flight prices have decreased to $49 across many dates including the date of my flights.

So I quickly toggle from the “$” tab to the “points” tab at the top of the screen and see that my flight has decreased to 2,468 points each way.

I followed the steps (listed above) for my refund and rebooked my flight.

In total, the process took a maximum of 5 minutes and I was refunded 13,204 points (18,140 – 4,936).

~13,000 points may not seem like a lot but remember, my roundtrip flight only cost me ~5,000 points. Theoretically, I just saved myself TWO ROUNDTRIP tickets between Atlanta and Washington D.C.

Let’s take this a step further, Southwest Airlines is a transfer partner of Chase Ultimate Rewards. In other words, you could apply for the Chase Sapphire Preferred card, obtain the current welcome bonus of 60,000 points and transfer those points to Southwest Airlines.

60,000 points looks very different when you can book roundtrip tickets for 5,000 points, huh!? 💡


Flexibility goes a long way in the world of travel, and having the option to be both flexible and frugal is as rare as an oasis in the middle of a desert. The good news is, seeing extra money (or points) in your account isn’t a mirage.

Have you rebooked an existing flight on Southwest Airlines to save money before? How much cash were you able to save?

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