Southwest runs sales almost all of the time, so you know you will be getting a good deal no matter when you book. This is because whenever a flight you have booked goes on sale, you can check your information and rebook if the price has dropped.
Checking My Flights
I have two trips coming up with flights booked on Southwest. I just checked both, and out of 4 segments, only one dropped in this sale. Even though it wasn’t much, that’s 581 points I can use towards another flight in the future. Booking flights in one way segments is the best way to take advantage of this deal. If you booked as a round trip, you would have to rebook both segments, and may not come out ahead. If you paid cash for your flight, you will get a voucher to use towards future travel.
This feature definitely sets Southwest apart. Add that to their generous two checked bags policy and their great customer service, I have a hard time even considering booking flights with other airlines.