The WORST Month to Book Southwest Flights (and Other Secrets to Finding the Best Deals!)

Signing up for credit cards through partner links earns us a commission. Here’s our full Advertising Policy.

Lyn writes about flying on Southwest at her GotoTravelGal.com blog and has a free guide that walks you step-by-step through how to earn the amazing Southwest Companion Pass.  The Southwest Companion Pass lets 1 person fly nearly free with you for up to 2 years!

I’ve asked Lyn to fill us in on what she’s learned about the best times to fly (and not to fly!) so far this year on Southwest.

Lyn:   Over the last few months, I’ve been tracking the best fares every week on Southwest from more than 30 destinations for my GotoTravelGal.com readers.  I post the new fares each Tuesday or Wednesday, because Tuesday tends to be the day of the week when airfares are the lowest.

Not only has this information been helpful to my readers (you can check out my Southwest deals page for this week’s best fares), but by watching fares week by week, I’ve learned a lot about Southwest pricing.  I thought I’d share that information in case it helps you book your spring, summer, and fall Southwest flights.

Plus, Southwest is notoriously harder to book and compare prices, because they don’t allow their fares to be published on any outside site like Google Flights, Expedia, etc.  You have to go to Southwest.com to check fares and book your flights directly.

Still, I LOVE Southwest!  Here are reasons to consider Southwest for your next flight.

The Worst Month for Booking Southwest Flights This Year

Currently, Southwest will allow bookings through November 3, 2018.  The airline releases new dates for booking every ~6 weeks or so, with the next planned release scheduled for May 31, 2018, for flights through January 6, 2019 (how are we talking about 2019 already?).

So far this year, 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 3 days available for booking, has shown some good deals.

When You Should 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 ~3 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 3-month mark, the deals usually aren’t there yet either.  There are, however, currently some good deals for August through October, though it may only be part of a Southwest sale.

That said, 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 points re-deposited into your Southwest account.

Here are 5 tips for how to know when a Southwest sale is a good one, because they have so many!

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

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 US!  🙂

Join the Cheap Southwest Flights Facebook Group

In addition to my Southwest Deals page updated weekly, you can join Go to Travel Gal’s Cheap Southwest Fares Facebook group where we share great Southwest fares we find with one another, so others migh be able to take advantage, too!

This helps overcome the obstacle of not being able to compare Southwest fares on other sites or get alerts when prices go down.

And remember to follow Million Mile Secrets on Facebook and Twitter so you never miss a deal!

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 3 months and 30 days ahead (you can cancel and re-book without penalty)
• Fly out of  Atlanta, Chicago, Denver, or Los Angeles!

What tips do you have for booking cheap fares on Southwest?

Never miss the best deals again!  Always check our Hot Deals page for an easy-to-digest list of the top rewards card offers!