The best & worst months to book Southwest flights (and other secrets to finding the best deals!)

October 16, 2019 by Million Mile Secrets Million Mile Secrets

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This story was originally published on March 15, 2018.

Over the last few months, I’ve been tracking the best fares every week on Southwest from more than 30 destinations. Not only has this information been helpful to my readers, but by watching fares week by week, I’ve learned a lot about Southwest pricing, which also affects Southwest award tickets. I thought I’d share that information in case it helps you book your upcoming Southwest flights.

This information could be especially useful because Southwest doesn’t allow their fares to be published on any outside site like Google Flights, Expedia, etc. You have to go to Southwest’s site to check fares and book your flights directly. Regardless, Southwest is always a reader favorite for many reasons, like the fact that they offer everyone two free checked bags and the ability to earn the Southwest Companion Pass.

We’re sharing tips on when to book your Southwest flights. (Photo by NextNewMedia/Shutterstock)

When to book Southwest flights

The worst month for booking Southwest flights

In collecting the data so far, the one month that rarely seems to have any good deals or a decrease in fares is – drumroll please – July. No surprise, really, because summer is one of the busiest travel times of the year.

However, every other month, excluding November, which only has three days available for booking, has shown some good deals.

The best months to book your Southwest flights

After studying the fare data for a few months, I’ve found that you’ll find the cheapest Southwest fares between three months in advance to no later than 30 days ahead. The best deals are usually found within this time frame.

Once the 30-day mark is crossed, nearly all of the low fares go away. That said, I have had readers tell me they checked the day of travel and found a better fare and rebooked, so you never know.

Also, if you get too far ahead of the three-month mark, the deals usually aren’t there yet either, unless they are part of a Southwest sale.

All that aside, the best time to book your Southwest flight is now because if the price drops, you can cancel your flight and re-book for free. You’ll get a refund of the fare difference (in the form of a travel credit, valid for a year) or have the difference in Southwest points re-deposited into your Southwest account.

The best cities to fly from

I’ve also learned there are just some cities that have way better fares than others. Lucky you if you live in one of these top Southwest cities, which continually have low fares to lots of destinations:

Atlanta
Chicago (Midway)
Denver
Los Angeles

The Mile High City has tons of cheap Southwest fares to cities across the U.S. (Photo by Darryl Brooks/Shutterstock)

Denver is by far the best, and I’m thinking of packing my bags and moving there just to take advantage of all the low fares to places all over the U.S.

Earn more Southwest points

The easiest way to rack up Southwest points is by earning a welcome bonus from Southwest credit cards:

And the good news is, the three personal cards are currently offering an increased welcome bonus of up to 60,000 points after meeting tiered spending requirements.

Earning bonuses from these cards will count toward the Companion Pass. So by opening one personal and one small-business Southwest credit card, you’ll have enough points to immediately qualify for the Companion Pass.

If you need help deciding among the cards, read our Southwest credit card comparison guide. Remember, you can only hold one Southwest personal credit card at a time, but you can have one or more business Southwest cards, in addition to a personal card.

Bottom Line

Finding the cheapest airfare deals on Southwest is easier if you keep these tips in mind:

Try to avoid July
Book right away, but keep an eye out for fare drops between three months and 30 days ahead (you can cancel and re-book without penalty)
Fly out of Atlanta, Chicago, Denver, or Los Angeles

Do you have any tips for finding the best deals on Southwest? Please share them below!

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