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

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 readers, but by watching fares week by week,we’ve learned a lot about Southwest pricing (which also affects Southwest award tickets). I thought I’d share that information to help 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 must 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, has shown some good deals.

The best months to book your Southwest flights

After studying the fare data for a few months, I’ve it appears that you’ll find the cheapest Southwest fares between three months and 30 days in advance. 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.

If you get too far ahead of the three-month mark, the deals usually aren’t available, 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

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. Right now the three Southwest personal cards have their highest-ever sign-up bonus. With the Southwest Rapid Rewards® Plus Credit CardSouthwest Rapid Rewards® Premier Credit Card, or Southwest Rapid Rewards® Priority Credit Card you’ll earn 40,000 bonus points after spending $1,000 on purchases within the first three months of account opening.

You can also earn a large welcome bonus on either Southwest business card The Southwest Rapid Rewards® Premier Business Credit Card comes with 60,000 bonus points after you spend $3,000 on purchases in the first three months your account is open. And the Southwest Rapid Rewards® Performance Business Credit Card comes with up to 100,000 points when you meet tiered spending requirements:

  • 70,000 points after you spend $5,000 on purchases in the first three months of account opening
  • 30,000 additional points after you spend $25,000 on purchases in the first six months of account opening

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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