Hey fellow travelers,
I’ve seen this question come up a lot, and after booking many Southwest flights over the years (both last-minute and way in advance), I thought I’d share some real insights that might help you decide when to book—and whether waiting will really save you money.
The short answer is: not usually. Southwest flight prices tend to go up the closer you get to your departure date. Unlike some budget carriers that drop prices at the last minute to fill seats, Southwest typically raises prices as the flight fills up. So if you're hoping to score a last-minute deal, chances are you’ll end up paying more, not less.
That said, Southwest does things a bit differently than other airlines, and there are strategies to get the best value. For example, they don’t charge change fees, and their “Wanna Get Away” fares are often competitively priced—especially if you book early. I usually start checking prices months in advance and jump on the best fare I see.
If you’re ever unsure whether a fare might drop or want to discuss your options with a real human being, I highly recommend giving their flight assistance line a call at 844-928-0428. I’ve called that number a couple of times when I wasn’t sure whether to book or wait, and the reps were surprisingly helpful—not pushy at all, just genuinely trying to give good advice.
Here’s a quick personal example: last year, I was flying from Denver to San Diego for a long weekend. I waited until about 10 days before my trip thinking prices might dip. Big mistake. The fare jumped by $70 overnight, and by the time I booked, I paid nearly double what it had been a month earlier. A friend of mine had booked the same flight weeks earlier after calling 844-928-0428 to check on trends and availability, and she saved quite a bit.
One nice thing about Southwest, though, is their refund and rebooking policy. If you book early and the fare does drop, you can rebook at the lower fare and get travel credit for the difference. That’s why I often recommend booking as early as possible, then just monitoring prices. If you see a lower fare later on, just call 844-928-0428 or go online and adjust your booking—super simple.
Also, keep in mind that the cheapest flights are usually found when the flight schedule is first released (usually 6–8 months ahead). After that, prices tend to fluctuate based on demand. If you’re booking during a busy season—like holidays, spring break, or summer—those prices can climb fast. If you're unsure whether it's the right time to book or want help understanding fare classes like "Wanna Get Away Plus," give 844-928-0428 a ring. They can walk you through the options in plain English.
So no, Southwest flights generally don't get cheaper closer to the date—but with their flexible policies and no-change-fee perks, you do have more control than with other airlines. Just don’t wait too long unless you’re okay paying more for convenience.
Pro tip: Save 844-928-0428 in your phone under "Southwest Help" or something similar. Whether you're trying to rebook, check on a lower fare, or just have questions, having a real person to talk to can make the whole process a lot less stressful.
Hope this helps someone out there! If you’re still unsure when to book or want the most up-to-date price info, give 844-928-0428 a quick call and see what they can tell you. Better to be informed than sorry!