Other blogs have written about this, including my good friends at Miles to Memories. (Also Danny Deal Guru, Dan's Deals - with a fairly long writeup, and Doctor of Credit, among others I'm sure.)
But it seems to me that many folks are missing out on just how generous the situation is right now!
I have NO IDEA** how long this is going to last, so I suggest jumping on making some bookings (maybe even speculative bookings?! - read below), ASAP.
As you may know, Southwest Airlines has a very generous change and cancellation policy in general. You can always cancel (or change) flights with no penalties, other than paying the difference in fare (if you change to a different flight). If you cancel a flight you pay for with cash, you get the funds back and have a year to use those funds (must use those funds for the same person, but on any routing). Even better, if you book with miles (and Southwest miles pretty much always have a value of 1.4 cents/mile towards the cash price), then you can cancel the flight and just have the miles go back into your account (and then you can book future flights for anyone with no time limit).
BUT HERE'S WHAT IS SO EXCITING RIGHT NOW! You can basically book any Southwest flight from point A to point B for the lowest price that ticket ever sells for! Just find the lowest price fare (for the same point-A-to-point-B, even if different routing) up to 30 days before or after the flight you actually want to take ... and that is your price!! (using the instructions below!) And this is available for any flights/bookings up through the end of October, so with the 30 day change, you effectively book any flight from today through near the end of November. Even for flights around Thanksgiving, which are usually expensive!
Another nice trick (pro tip!) is if you need to fly in the next week. Usually Southwest fares go WAY up within a week. But right now you could book a "dummy" flight for more than a week from now ... and then follow these instructions ...
Once you find what appears to be the cheapest flight between point A and point B (scanning multiple dates for the cheapest price), within 30 days of your desired flight, book it. (There's really NO risk if you're paying with Southwest miles, since you can easily cancel. If you're paying with cash, you will hopefully want to know if this deal is still alive.** Otherwise, if you go to make the change, and find the deal is dead, then you might just have to cancel the "dummy" reservation and you'd have one year to use those fund.)
Then once you have that booked, go into this "dummy" reservation in your Southwest account and click on "CHANGE" reservation (or just click the "CHANGE" link on your screen immediately after you book the "dummy" reservation). This is what you will see:
After you hit "accept & continue", you will be given the option to choose a different date (plus or minus 30 days) for the same flight from point A to point B. Once you choose your actual preferred date, you will see a screen that look like this:
As you can see, you'll also be able to play around with the dates on this screen (using the tabs at the top of the page). But once you're sure you're on the correct date, you'll see that you can choose any "Available" flight (even if the routing from point A to point B is different, or even going from a 1-stop or 2-stop flight to a nonstop flight ... which are often more expensive on Southwest!). And you will see that making this change is FREE! (Make sure you get to the final "change" screen and process the change, and then look for a confirmation email.)
If you end up needing to cancel these flights, the cancellation/change policy remains the same. As discussed above, you'll either get your miles back or cash "credit" to use on a future SW flight within the next year.
So hopefully that makes sense for why NOW is the time to even potentially book speculative trips for the next few months.
Why is Southwest doing this? Honestly I'm not 100% sure. They've been doing it on a rolling date/calendar basis for quite a while now, as kind of a way to make up for the fact that they've had so many flight/date/time/routing changes due to the Boeing 737 MAX issue. But right now the time frame they are allowing is so wide and generous, that I have to wonder if it is Covid-19 related. Again, I don't know how long this will be around, but it sure is generous ... so jump on it!
If you're asking ... how do I get these Southwest miles you're talking about? Well, besides earning them for flying Southwest (on cash bookings), you can also get them from credit card spending and/or sign up bonuses. If you have (or want to get) Chase credit cards that generate Chase Ultimate Rewards points, these can be converted into SW miles on a 1:1 basis. Or you can get Southwest Airlines credit cards from Chase (if you're interested, please consider using my referral link HERE) to get a big mileage signup bonus and earn miles. You could also consider going after the Southwest companion pass (which I previously wrote about HERE six years ago!! - the terms have changed some, but it is still available).
**I will attempt to notate this deal as being "DEAD" whenever I hear it has gone away. I don't know if it will be alive for another day, or two, or more. Or if the dates available for booking/changing will change. But just know that if you're booking the "dummy" fare with cash, you are taking some "risk" that the deal (or available calendar/change dates) will have gone away. And you might get stuck cancelling your cash-booking and just having a credit to use within a year.
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