The Secret to Scoring the Cheapest Southwest Flights

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Do you believe that decades ago, I used to hate Southwest Airlines? I thought it was just a mess of an airline and way too chaotic.

Fast forward to the past decade and it’s my preferred airline to fly. I love how easy it is to cancel or change your flight. I love that they’re still not charging for checked bags (even though we only do carry-on bags nowadays). I love how the flight attendants generally try to put on a happier face than you might see with other airlines. I love that I can order water or ginger ale and get snacks without getting nickeled and dimed like the cheapo airlines.

And I’m indifferent about the open seating concept. The whole idea is sort of odd to me but it doesn’t matter to me either. We just do our thing. I don’t splurge for the EarlyBird Check-In either. I just set an alarm for a little over 24 hours before check-in and roll with that. We usually score higher A group or lower B group seating and life is good. And with the Southwest credit cards we tend to have, we can usually get upgraded boarding when we want.

So life is good… except that Southwest Airlines used to be the cheapest airline and that’s rarely the case anymore. Obviously, you can find cheaper prices on ultra-low-cost carriers like Frontier, Allegiant, Spirit, and Breeze, but there are trade-offs in what you get. Plus, they might only fly one flight from A to B per day or even just a couple of times a week. So if there’s a cancellation for your flight, you’re really up a creek!

That’s not a knock on these carriers. We use them as well, as long as the flight duration is no more than a few hours (long flights on those seats are rough) and if getting to our destination on time isn’t absolutely critical.

On the other side of the coin are the other big airlines like Delta, American, and United. They all have pros and cons, but I’ll take Southwest if the flight prices are the same as the others. The problem is that prices can be all over the map. Sometimes you can find deals on Southwest and sometimes you can’t.

But the question is – how do you get the cheapest Southwest flights?

With our big year of worldwide travel well underway, I’ve been booking flights left and right. And I’ve recently figured out a strategy that seems to be a huge win in finding the cheapest Southwest flights. But not just the cheapest Southwest flights, but the flights we want to choose before they’re booked up.

Interested? You should be – if you like flying Southwest Airlines, this strategy can save you a ton of dough…

Optional: Leverage credit cards and the Southwest Companion Pass

This isn’t the secret, but it’s worth starting by discussing something you likely already know. One of the best ways to score the cheapest Southwest flights is by utilizing travel points.

If you’re spending points on travel, you’re saving the dollars that would have been spent otherwise.

That’s a gimme, but most folks tend to think that the only way to earn frequent flier miles is by flying on that airline. While that can definitely add to your stockpile on hand, most of our points come from credit card sign-up bonuses (and the spending to get those bonuses).

I applied for and got the Southwest Rapid Rewards Performance Business card in November. The sign-up bonus gave me 80,000 points along with the 5,000+ points for the spending to get that bonus. I also applied for and got the Southwest Rapid Rewards Priority card later in the month. That gave me 40,000 points and 3,000+ points for the spend to reach the bonus.

With just two credit card sign-ups, I was able to bank over 128,000 points.

We saved a lot of our spending for this because getting the 125k points was important. Some of these points were earned in 2024 with the majority earned in 2025. With the annual 10k Companion Pass “boost” from Southwest in January though, that gave us enough points to get the Southwest Companion Pass – good until 12/31/26.

The reason why this is so important is that it means that I can have a companion (my wife, Lisa) fly with me for free on every single flight I book from now until the end of 2026.

For our family of 3, instead of paying for 3 people for each flight we take over the next two years, we now only pay for 2. That shaves 1/3 off the price of every single booking we make. The more we fly, the more we save.

Additionally, we still have all those accumulated points to pay for me and Faith on almost all our flights. So that makes the flights completely free (except for taxes). And, of course, that means we’re using fewer points to book each flight, which spreads them out to even more flights we can take.

To read more about earning the Southwest Companion Pass, check out my post, Southwest Companion Pass: Why Now’s the Best Time to Act.

Right now, you can get the Southwest Companion Pass even easier. Chase is offering the Companion Pass for free by signing up for a single credit card and spending $4,000 in the first three months. The Pass is good through 2/28/26 so you can get it to use for almost a year with minimal effort… not too shabby!

The three cards with this offer are the:

• Southwest Rapid Rewards Plus Credit Card
• Southwest Rapid Rewards Premier Credit Card
• Southwest Rapid Rewards Priority Credit Card

You can see more information about these cards here. My recommendation would be to apply for the Priority card (that’s the one I have). Although it’s got the highest annual fee of the three, it comes with the most perks, including a $75 annual travel credit, which offsets the fee to be about the same as the cheapest card.

And if you’re looking for a fantastic way to manage your credit cards and bonuses and to help you find the right cards for your specific needs, check out Travel Freely. It’s absolutely free. It’s what I use to help us track our cards and find new ones.

Accumulating points or getting the Companion Pass isn’t the secret sauce to the cheapest Southwest flights, but it’s a fantastic way to fly for free or close to it! That’s why I thought this section was necessary.

So, what’s the real secret then?

The secret to the cheapest Southwest flights is…

The secret to getting the cheapest Southwest flights and getting the best available flights comes down to one thing:

Buy early and then reimburse yourself over time.

Wait, what? Doesn’t sound too exciting, does it?

It took me a little time to figure this out, but here’s why this is such a big deal.

If you’re like me, normally, you keep an eye on flights and when you notice the price drop to something you deem reasonable, you book the flight. Domestic flights, for example, typically drop to their lowest prices about 6 weeks before their scheduled departure. When flight schedules are opened up (usually about 10 months in advance with Southwest), flight prices are usually pretty high. That’s the worst time to book, right?

Wrong.

Southwest has an important detail in its rules that makes this the optimal time to buy:

You can change or cancel your reservation right up until the day of the scheduled flight.

Here’s why this is so valuable. If you book your Southwest flight as soon as you know you need the flight – especially if the schedule has just opened up for bookings – you get the pick of the lot on which flight you want.

Southwest makes it extremely easy to “change” your flight to the same one and recoup the cost difference with the new lower price. So the strategy is to take advantage of this to ensure you get the best flights and the cheapest Southwest flights.

Did you ever notice that when you wait for the cheapest Southwest price before you buy tickets, many of the best flights are already fully booked?

That’s no longer an issue if you book right off the rip. You can choose the flight times that make the most sense to you. Even if the price is too high and doesn’t go down much later, you can always change your flight to a less expensive one later.

But chances are, the price will go down – and maybe by a lot of money. My rule of thumb is that when I book a Southwest flight, I select one where I’m comfortable with the price as is. That way, if the price doesn’t go down, we’re still in good shape.

However, I’ve yet to see a time when the price didn’t drop.

The key is that Southwest isn’t going to tell you when the price drops – you need to do this manually. Even though it’s easy to do, if you know you’re someone who won’t routinely check for price drops, then this whole idea isn’t for you.

You can use something like tracked flights on Google Flights to help notify you when prices are lower, but I don’t think you even need that for this.

NOTE: Bear in mind, that if you book a Wanna Get Away or Wanna Get Away+ fare, you get a fare credit rather than money back to your credit card. If you’re someone who travels enough on Southwest though, you can turn around and use that credit for your next flight. ** Thanks to Rosie in the comments for reminding me about this one!

This strategy works whether you book your flight with dollars or points (keeping in mind the note just mentioned), so you’re good either way.

The bonus to using points when you can, however, is that you’re not tying up actual money while you wait for the price to drop. That’s why leveraging credit card travel rewards is so useful.

Just from the travel we’ve booked for this year, I’ve already gotten back hundreds (maybe into the thousands) of dollars over what I initially paid. Funny enough, I’ve gotten good money and points back more than five times just since I started writing this post.

So now that you know the secret to getting the cheapest Southwest flights, I’ll walk you through how to check for cheaper flight prices and get some of your hard-earned money or points back.

The process works differently if you have the Southwest Companion Pass and there’s a little more involved (not much). So I’ll take you through the steps if you don’t have the Southwest Companion Pass first and then again if you do have the Pass.

As a side note, you’ll see that all our flights are one-way trips. Always book one-way tickets. It used to make sense to book round-trip airfare because it was much cheaper than round-trip. Now, it’s almost always the same price. Having one-way tickets makes changes and cancellations much easier.

Plus, if for some weird reason you were to miss the first flight of a trip, the airline would automatically cancel your entire trip if you had booked it round trip. With a one-way ticket, you avoid all that.

Ok, now let’s go through how to reclaim some money or points on Southwest!

Bear in mind that about two days after I took all these screenshots, Southwest overhauled their app (of course!) – at least on Android. Everything still matches up but it might look slightly different if you got the new version of the app. You can also do these steps on the web, but I’ve found it to be simpler to do them on the app so that’s what I’m going to show you.

Getting money back without the Southwest Companion Pass

Without the Southwest Companion Pass, finding cheaper fares and claiming the price difference is ridiculously easy. All you need to do is open up the app and go into the trip you want to check for lower prices on…

Then you’ll click on the “Change” button to check for cheaper options:

Now you need to select the flight you want to look at. If you’re like me and only booking one-way flights, you’ll have just one option like you see here. But If you have a round-trip flight, you’ll want to select just one leg of the trip, go through the process, and then do it again with the other leg of the trip…

That’ll take you to a screen where you specify where and when you’re traveling. Assuming you plan on keeping the same date of travel, you can leave everything as is and click on “Find Flights”:

Now we get to the fun part! At the top of the screen, you’ll see your current flight. Somewhere in the list of flights below, you’ll find the same flight listed. Assuming you want to keep those times, that’s the one you’re looking for…

What you care about here is simply looking at the price (or points). If it’s zero or it’s got a plus sign in the amount, leave it alone, and call it a day. That would mean there’s no change in the price or you’d have to pay more to rebook that flight. Call it a day on this one, back out, and check another flight if you want.

But if it’s got a negative sign, that’s the jackpot! You’ll see that our flight dropped $50 (per person!). Select the flight to move on with the rebooking.

On this next screen, you choose the fare class that you want. In my case, we’ll just stick with the same class as we had booked before:

Now, you’ll see a wrap-up of what you’re rebooking. Notice that I’m getting $100 back in total from these two minutes of work…

On the review screen, you’ll choose how to be refunded. You can select the original credit card (unless it’s a Wanna Get Away or Wanna Get Away+ fare) or let Southwest hold the money for a future flight. Although most of the time I’d recommend choosing the original credit card, we’re working on the minimum spend for another credit card (the Citi Strava Premier card) so we don’t want money coming back onto our card right now. And we plan to book more flights relatively soon, so I’m choosing the option for them to hold the money…

If you’re happy with everything, click “Make these changes” to complete the rebooking, and BOOM, you’re done…

And just like that, in a matter of only a few minutes, you’re helping to ensure you’re getting the cheapest Southwest flights. And the more you do this, the faster you’ll be at the process. Pretty simple, right?

Getting money back with the Southwest Companion Pass

You saw how easy the process above was, but when you’re using the Companion Pass for a flight there’s just a small bit of extra work involved. That’s because you can’t easily check if the price dropped or change your existing flight with the companion attached to the reservation. And you don’t want to drop your companion off the reservation just to check it, because you’ll add unnecessary transactions into the mix. You might even lose that person’s seat if it’s a full flight and someone else books the flight while you’re checking.

So instead, I’ll take you through the way I do this. It only adds a couple more minutes to the process but it’s a lot safer and smarter.

The first thing you want to do is keep track of your flights in an easy-to-use note. We want to keep this simple, convenient, and straightforward. I keep mine in a pinned Google Keep note (until I’m ready to move off Google Keep for more privacy). I like it because I can get to it easily from my phone or my computer. Here’s the actual note I have right now with the days blurred out so you don’t follow me around the world like some crazy person!

This is not where I keep everything for our trips. I use Kayak Trips to easily organize and store all the details in one place. It gives me alerts for changes and everything and it’s free. I’ve been using Kayak Trips for over a decade and love it!

These flights are only the Southwest flights – that’s all we want on here. We’ve got a handful of flights on other airlines that don’t make it to this list… one busy travel year!

I put just enough information regarding each flight in it so I could find the matching flight and how much I spent in dollars or points to book the flight. Yes, you can dig this up in your reservation email, but that’s a pain and won’t reflect what you paid after future price drops you’ve recouped. That’s why the note works nicely – it’s fast and easy.

You’ll notice I’m calling out the $329/pp for you on that note. That’s because that’s the flight and price we’re looking at in this example.

The first thing you’re going to do is go through the motions as if you’re booking a new flight…

If you booked round-trip, only focus on one leg at a time for this and then you can go through this process for the other leg after. So choose “One way” and all the same details. Select 1 passenger even if you have more than one person. That’s because sometimes there are different prices for multiple passengers (i.e. there might be 1 seat left at $200 and then more seats available at $300). It’s good to know this, which you’ll see shortly. And then select $ or points depending on what you booked the original flight with. It should look something like the screen above and then choose “Find flights.”

What you’re looking for is your original flight (though you can look at other flights if you see something better). Here’s the 12:10pm flight we have booked that you saw on my note…

I can see that it’s $279 per person whereas my booking price was $329. That’s a $50 difference per person, which comes out to be $100 total for me and my daughter. My wife doesn’t count for this because she’s the free companion.

Ok, now we want to back up to the previous screen and make sure that we see if that’s the same price for more than one person. Even though I’m only going to be changing the flight for two people, I like to choose more people (3’s a nice number) just to ensure there’s some wiggle room with available seats. This gives me a better idea of the price for multiple people and is important since we’ll be dropping our companion off the reservation. We need to make sure there’s enough room on the flight to put the companion back on should someone else book our same flight in the meantime…

After clicking adjusting the number of passengers and clicking “Find Flights”, we can see that nothing’s changed…

That’s good! That tells me that there are at least 3 available seats (not even counting ours) on this flight. I’m comfortable with that for a couple of minutes, so let’s give our companion the boot.

Back out of where you are and go into the trip details for your booked flight that we’re looking at…

Then, click on the “Details” button for your companion on the trip…

Time for the scary part… click “Cancel” for your companion’s reservation…

Then you need to choose what you want to do with the credit from the taxes paid on the Companion Pass reservation. I chose “Hold for future use” but you can also choose to refund it back to your credit card…

And just like that, you’ve kicked your companion off your flight reservation. Who needs ’em anyway, right?!

At this point, the steps are identical to what I discussed you would do if you didn’t have a companion (except at the end). But, let’s go through them just to make it a little more fluid…

Go back into your trips and select the one you’ve been working on…

Click on the “Change” button:

Select the flight you want to look at. If you’re like me and only booking one-way flights, you’ll only have one option like you see here. But If you have a round-trip flight, you’ll want to select just one leg of the trip, go through the process, and then do it again afterward with the other leg of the trip…

That’ll take you to a screen where you specify where and when you’re traveling. You can leave everything as is and click on “Find Flights”:

At the top of the screen, you’ll see your current flight. Somewhere in the list of flights below, you’ll find the same flight listed. Assuming you want to keep those times, that’s the one you’re looking for:

We already know that it was $50 cheaper per person so this screen matches up to what we expected. Select the flight to move on with the rebooking.

Now, choose the fare class that you want. In my case, we’ll stick with the same class as we had booked before:

You’ll see a wrap-up of what you’re rebooking. Notice that I’m getting $100 back in total from only a few minutes of work…

On the review screen, you’ll choose how to be refunded. You can choose the original credit card (unless it’s a Wanna Get Away or Wanna Get Away+ fare) or let Southwest hold the money for a future flight. Although most of the time I’d recommend choosing the original credit card, we’re working on the minimum spend for another credit card (the Citi Strava Premier card) so we don’t want money coming back onto our card right now. And we plan to book more flights relatively soon, so I’m choosing the option for them to hold the money.

If you’re happy with everything, click on “Make these changes” to complete the rebooking and then BOOM, you’re done (mostly)…

One more small detail – it’s time to add back your companion onto the reservation or they’re not going to be a happy camper!

Head back into your trips and choose the one we’re working on once more…

Choose the “Add companion” button…

Review the info to make sure everything is correct and click “Continue”…

Time to pay the taxes! Choose your payment and then click “Purchase”…

Your partner in crime is now back on your reservation and life is good again!

Here’s the last important step. Update the price per person on your saved note to what you’ve now knocked the ticket price down to for this trip…

The reason this last step is important is because you’re not done. if you want to ensure you’re getting the cheapest Southwest flights, you want to do this whole process routinely. And the more you do this, the faster you’ll be at the process. I can now cruise through all my flights in less than 5 minutes and then spend another 5 minutes on a flight to grab any of the drops in price that have come up.

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Hopefully, this little travel hack can help you get the Southwest flight you want at the best price.

Because it’s so easy, I try to check on all my flights daily. But that’s up to you how often you want to do this. The cheapest Southwest flights are going to come and go though so the more often you check it, the better the chance of snagging the price drops before they disappear.

If you enjoyed this post, why not jump on the mailing list? I’ll keep you up-to-date with new posts and share some things I don’t talk about in the blog. Plus, just for signing up, I’ll send you an email with a bunch of useful spreadsheet tools I created and use myself that I think you’ll appreciate…

Now, go and save some money with this little trick so you can travel even more!!

Plan well, take action, and live your best life!

Thanks for reading!!

— Jim