By far the most common question I see in the Cheap Southwest Fares Facebook Group for email subscribers is: When is the best time/should I book a flight to [FILL IN THE BLANK DESTINATION] for [FILL IN THE BLANK DATES].

And there is an easy answer for every single version of this question.

The answer is NOW!

Because Southwest lets change your flight with no penalty and cancel a flight and get a one-year travel credit if you purchase a Wanna Get Away fare or get a refund if you redeem points, there’s no reason not to book your flight as soon as possible.

If you know you can re-book with no change fee and get a travel credit or refunded points if the price goes down, then you should book now.

Generally, the further out you book on Southwest, the better.

Southwest typically releases flights for booking about six to eight months ahead, and my readers tell me when you book as soon as those flights are released (like 5 a.m. on the day of release as soon as they come out!), they get the best deals. Many have said when they checked just several hours later, the price went up.

So bottom line: There’s no time like the present.

2 Other Considerations When Booking Southwest Flights

Kids Southwest Plane Grand Cayman

I have found in general that flights tend to be lowest on Tuesdays, so if you want to wait until the next Tuesday to book once you’ve decided on a destination and dates, that’s fine, but otherwise book as soon as you can.

Lastly, sales are always a good time to book Southwest flights. They are not always their lowest prices, but they are lower than when they’re not on sale :).

You can always find the latest Southwest sale here.


  • Lyn Mettler

    Lyn Mettler is a longtime travel writer for US News & World Report, USA Today 10Best and The TODAY Show who created Families Fly Free, a program which teaches families her simple system to use travel rewards to fly for free.

    View all posts