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

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This story was originally published on March 15, 2018.

We often track 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.

The coronavirus has upended this data in large part, but many truisms still hold. The 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 

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.

Southwest response to COVID-19

In the wake of the novel coronavirus, Southwest has extended the expiration date of travel funds (which normally expire one year from the date of purchase). Any travel funds that have expired or expire between March 1 and September 7, 2020, will now be extended until September 7, 2022. And any travel funds created because you cancel a flight between March 1 and September 7, 2020, will expire September 7, 2022.

Also, members who have travel funds that are set to expire or funds that are created between March 1, 2020 and September 7, 2020 will have the option to convert their travel funds into Southwest points at the same rate you would be able to purchase a ticket with points.

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!

For the latest tips and tricks on traveling big without spending a fortune, please subscribe to the Million Mile Secrets daily email newsletter.

Joseph Hostetler is a full-time writer for Million Mile Secrets, covering miles and points tips and tricks, as well as helpful travel-related news and deals.

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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