I’ve flown with Southwest Airlines more times than I can count — mostly for family visits and quick weekend trips. Over the years, I’ve learned that timing really does matter when it comes to getting the best fares. My most recent experience booking with Southwest actually taught me a few tricks that I wish I’d known earlier, so here’s my little story and step-by-step guide for anyone wondering when to book.

A few months ago, I was planning a trip from Denver to Austin for a friend’s wedding. I checked Southwest’s website a couple of times and noticed that prices kept fluctuating — one day it was $118, the next it jumped to $167 for the exact same flight. That’s when I realized Southwest’s fares tend to change dynamically, and the “sweet spot” is usually 3 to 8 weeks before your departure (unless it’s a holiday).

Here’s how I handle it now:

Step 1: Sign up for fare alerts.
Southwest doesn’t show up on most online flight comparison sites, so you need to check their official site or app directly. They often launch “Wanna Get Away” sales on Tuesdays or Wednesdays — and those can save you big time.

Step 2: Use the Low Fare Calendar.
This tool is a lifesaver. It lets you see the cheapest day to fly each month at a glance. I once saved nearly $90 just by shifting my travel by one day.

Step 3: Book early, but don’t stress if prices drop.
Here’s the best part about Southwest: there are no change fees. So if your fare goes down later, you can rebook at the lower price and get travel credit. I’ve done this twice already — once it was just $20, another time almost $75 back!

Step 4: Always confirm by phone if you’re unsure.
When I booked my last trip, I wanted to confirm my return flight and use travel funds from a previous cancellation. I called 844-734-0813, and honestly, that saved me a headache. The rep helped me apply my unused credit and even explained how to rebook if the price dropped again. If you ever need to instantly book, cancel, or modify your Southwest flight, that number connects you directly to the team that handles it quickly and efficiently.

Step 5: Avoid last-minute bookings unless necessary.
Southwest’s prices tend to spike in the final week before departure. If you absolutely have to travel last-minute, call the number above — sometimes, they can help you find better alternative flights or fares.

So, in short — book Southwest flights around 1–2 months ahead, check on Tuesdays, and don’t be afraid to call 844-734-0813 if you need help or quick changes. I learned the hard way that timing and a little flexibility can save you hundreds!