There is an art to snagging cheap Southwest flights. Watch this 3-minute video above or read the article below where I explain some of my top tips for finding cheap flights on Southwest that I’ve personally learned flying Southwest since 2015.

How to Find the Cheapest Southwest Flights

If you’re planning a trip and want to stretch your points (or dollars) further, Southwest Airlines is hands down one the best deals going. But like with any airline, snagging the lowest fares takes a bit of strategy.

Over the years, I’ve learned a handful of simple tricks that can help you consistently find cheap Southwest flights — and save enough to take extra trips each year.

1. Start With the Low Fare Calendar

The very first place I go when searching for flights is Southwest’s Low Fare Calendar. This handy tool lets you see fares across an entire month — or even multiple months at once. Instead of checking dates one by one, you can instantly spot the cheapest days to fly.

Over time, you’ll also get a sense of what “low” really means for your favorite destinations. For example, maybe you notice fares to Orlando sometimes dip as low as 6,000 points one-way, while to Denver they often bottom out around 5,000. Once you know those rock-bottom numbers, you’ll recognize a deal when you see it — and that’s the time to book.

I recommend checking the calendar about once a week on Tuesdays, if possible. After a month or two, you’ll have a clear picture of what’s a regular price and what’s a DEAL.

2. Fly Midweek or at Off-Peak Times

Like most airlines, Southwest tends to charge less for flights when fewer people want to travel. That usually means…

• Tuesdays and Wednesdays: Historically the cheapest days of the week to fly
• Early mornings or late evenings: If you don’t mind a sunrise departure or a late-night arrival, you’ll often save big

If you can weather these schedules, considering these shifts can make a big difference. Sometimes adjusting your trip by just one day can cut your points (or cash) cost in half. I can’t tell you the number of times my family has saved TONS of points simply by shifting to a Tuesday to Tuesday or a Tuesday to Wednesday flight!

3. Consider Alternate Airports

Another way to save is to look beyond your closest airport. My family lives about 2.5 hours from Chicago Midway. That’s not exactly around the corner, but if I can save enough points for another entire trip by flying out of Midway instead of our hometown airport, the drive is worth it to us!

If you live within a few hours of multiple airports, always compare. The difference can be hundreds of dollars — or tens of thousands of points — especially for popular vacation destinations from these airports, such as Florida, Mexico or the Caribbean.

4. Always Book in Points (and Rebook if the Price Drops)

Here’s one of the best-kept secrets about Southwest: you can rebook your flight if the price drops (even with the Basic fare added in 2025) — and if you’ve booked in points, those points go right back into your account. No penalties, no change fees.

That’s why I always recommend booking Southwest flights with points instead of cash. Prices fluctuate constantly, and it’s not uncommon to see your same flight fall by thousands of points in the weeks or months before departure. When it does, just rebook and pocket the difference.

Inside my Families Fly Free membership, I walk members step by step through exactly how to do this, because it’s one of the easiest ways to maximize your travel savings and we literally save tens of thousands of points (enough to take another trip or 2!) every single year.

5. Learn the Insider “Hacks”

Beyond these basic tips, there are always little-known tricks that can save you even more on Southwest. These “hacks” change over time, so you need to stay up-to-date on which ones are currently working and how to apply them.

For example, members inside Families Fly Free have saved hundreds of thousands of points by combining the strategies above with current insider hacks. That often means doubling (or even tripling) the number of trips they can take each year without spending a dime on airfare.

Why This Matters

At the end of the day, cheap flights aren’t just about saving money. They’re about creating more opportunities to travel — more weekends at the beach, more trips to visit family, more once-in-a-lifetime adventures you wouldn’t otherwise take.

When you know how to find and rebook Southwest flights at their lowest prices, your travel budget stretches dramatically further. And when you add the Southwest Companion Pass or other travel rewards into the mix, my members save an average of $7,500 in their first year of implementing my strategies.

Take the Next Step

You can start applying these tips right now on your own — check the Low Fare Calendar, look at midweek flights and book in points whenever you can. But if you’d like a proven system (plus ongoing support and insider updates) that makes the process even simpler, that’s exactly what I provide inside my Families Fly Free membership.

I keep you updated on the latest hacks, walk you through rebooking step by step and even build you a personal travel rewards plan. Members regularly report saving $5,000–$10,000 or more on their trips each year — and they often take more trips than they ever dreamed possible so they can make more family memories before their kids, or grandkids, leave home.

Bottom line: Cheap Southwest flights are out there — you just need the right tools and strategies to find them. With these tips, you’ll be well on your way to saving thousands of points (or dollars) and taking more trips with the people you love.

Read More:

• ARTICLE: 7 Consistently Cheap Fares on Southwest
• PODCAST: Comparing the Southwest, Alaska and Delta Companion Pass
• ARTICLE: 101 Ways to Earn Southwest Points