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Southwest works very differently than most other US carriers. Instead of having their flight schedule available 330 days out, they push out their booking window in batches a few months at a time. Up until now, flight were only available through Aug. 10, 2020, but as of just a few minutes again, Southwest extended their reservation schedule through Oct. 30, 2020. This means you can now go ahead and book the rest of your summer vacation flights and even into the fall.
Related: Up to 100,000 bonus points with Southwest Credit Cards
From past experience, booking the day the schedule is released could get you the best prices for peak travel dates. For this release, this could mean Labor Day weekend and Columbus Day weekend.
Since Southwest has no change or cancelation fees, you can book now and cancel later. This also means if a Southwest flight drops in price, you can get the difference back simply by going through the process of "changing" your flight. If you pay for your flight, you'll end up with a Travel Fund voucher if you cancel or if the price goes down. But, if you use points, the points will simply go back into the account they were booked from. Here is the break-down:
If you are going for the Southwest Companion Pass, where you can fly a companion 2-for-1, you can still book your flight now and add your companion later. Once you actually receive the pass, you can go ahead and add on your companion to your reservation. Remember, your companion flies for free plus taxes/fees. This is a great way to take advantage of todays prices with the Southwest flight schedule release and have your companion fly for free.
Reminder: Points earned from the five Southwest credit card welcome offers will count towards earning the Southwest Companion Pass, but make sure to time your application accordingly.

We are a huge Southwest family, which means I will be making many flights this morning with my Southwest Rapid Reward points. I am personally making speculative vacation plans for the end August when the kids are still out of school and for Columbus Day weekend. Typically, I do not love flying over the summer since we live in New England and summer is the best time to stay in the local area. But, with our beginning of the summer plans being in limbo due to Coronavirus, we might break our typical rule and travel in August.
Also, if you are wondering when the next schedule extension is taking place, currently it is set for June 3, 2020. At that point, you'll be able to book your Thanksgiving, Christmas and New Years vacations.
Where did you book?

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