Cyber Sale: Southwest Airlines Flights From $39 (or 2300 points)

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.

But remember those new flights to Miami, Palm Springs, and Telluride? …they’re on sale for $39. However, time is of the essence as you have to purchase your ticket before 3 December 2020, 11:59 p.m. Central Time.


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.

But did you know that if you book a Southwest flight and the price decreases between the time of booking and your departure, Southwest will credit the price difference back to you? 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 price difference between your current reservation and the new one you’re about to make.

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 head directly 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.


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?

Let’s get straight to the point…some of the links on this site pay 1TattedPassport a referral bonus for anyone that is approved. For our complete advertising policy and details about our partners, please click HERE. Although using the links are completely optional, we are eternally grateful when you do.

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