How often do I check Southwest fares?  If I have a flight booked, most of the time, it’s every day! 

Or, at a minimum, once a week on Tuesdays when there tend to be the lowest cheap Southwest flights.

Because I keep such a close eye on Southwest fares, I’ve really gotten to know which ones are regularly cheap, and I’m going to tell you about the ones I see ALL the time.

You can almost count on them like clockwork!

If you can score cheap flights on Southwest AND you hold the Southwest Companion Pass, which lets one person fly FREE with you for up to TWO years, you get double the value out of this rock-bottom fare.


Want to learn the EASY way to fly for free by collecting and redeeming travel rewards? Join us in Families Fly Free, the premier online travel club where you can learn our SIMPLE, step-by-step system and save thousands of dollars in the process, while enjoying 1-on-1 support, a vibrant community and timely travel webinars and alerts. It's helped hundreds of families and thousands of people be able to travel MORE while spending less -- all while making priceless memories with their families.


See what members have to say...



Why You Need to Know What’s a Good Fare Price for a Destination

But first, I want to share with you the importance of knowing what a low fare price is for a destination you regularly fly to — or that is on your radar.

Southwest schedule open January, February, March
Credit Stewart Seeger Flickr

This is how couponers, one of which I used to be, score such good deals.

They track prices and KNOW what a good price is for a particular item. 

When that price rolls around, they make the purchase AND pair it with a coupon.

That’s how they get rock bottom prices and sometimes even free goods.

So, it’s important for you to have an idea of what a low fare looks like for you between key destination pairs.

And during this pandemic is a great time to study those fares, as they are almost at rock bottom.

That way, you’ll KNOW when there IS and ISN’T a good price available from Southwest when you’re ready to travel again.

Because Southwest often has sales that really aren’t so great (here’s how to know when a Southwest sale is a good one!), this will help you know if your destination pair is truly on sale or not.

Got it?  Good! 🙂  Now on to the cheap flights on Southwest…


7 Consistently Cheap Southwest Flights

southwest engine vertical

While flights and fares change, there are just some city pairs that seem to ALWAYS be cheap.  Sometimes the fares are cheaper than others, but they are still always pretty low.

Here goes…

1. Cincinnati, Ohio, to Baltimore/Washington, D.C.

Southwest cheap flights

This route has gotten as low as $39, but is more typically $49-$69 during ordinary sales.

But I almost ALWAYS see it super cheap.

This is hands-down THE cheapest city from which to fly to D.C. on Southwest! 

So if you’re close to Ohio (like we are in Indianapolis) and want to visit the nation’s capital, consider making the drive to Cincinnati.


2. Atlanta to Nashville (and vice versa)

Nashville top 2017 destination
Credit: Nashville Convention & Visitors Corporation

Prices for this route tend to hover around $49 at its lowest or more regularly between $57-$85.

Southwest added 5 non-stops daily from Nashville to Atlanta in 2018, as apparently this is a popular route! 

Check out these 53+ Things to Do in Atlanta You Should Not Miss!


3.  Louisville to Chicago

Wrigley Field Chicago Cubs World Series
Louisville to Chicago is lately a cheap flight on Southwest

The fare usually hangs between $69-$89.

Head to the Windy City for a big city getaway. 

Here are my tips for things to do in Chicago during the summer.


4.   Ft. Lauderdale to Grand Cayman

Cheap Flights Southwest
My family at Rum Point on Grand Cayman Spring 2018

At its lowest this fare is about $59 and you’ll see it creep up to $79 at times.

We took advantage of this cheap flight over one Spring Break, taking an inexpensive flight on Allegiant to get from Indianapolis to Ft. Lauderdale and then using ~2,200 points per flight per person (with one of my four family members flying free on my Southwest Companion Pass) to fly Southwest to Grand Cayman for a total of about 13,000 points and $260 per person.

[Here’s how we did it]


5. St. Louis to Atlanta

Atlanta Centennial Olympic Park Southwest Sale
Visit Atlanta’s Centennial Olympic Park and check out the Coca-Cola Museum, Aquarium and more with a cheap flight from St. Louis!

This is another one that is inevitably cheap.

We saw some AMAZINGLY cheap fares out of St. Louis in 2018, like 700 points per way cheap, but those have since gone away.

Atlanta hovers around $69-$89 from St. Louis.


6. Anywhere in California to Anywhere Else in California 🙂

Big Sur California Bridge

Southwest prices regularly go down to $39-$59 between California city pairs from nearly any one to any other one.

You can fly into and out of the below California airports on Southwest:

  • Burbank
  • Long Beach
  • Los Angeles
  • Oakland
  • Ontario
  • Orange County
  • Sacramento
  • San Diego
  • San Francisco
  • San Jose


7.  Tampa to Havana, Cuba

cheap southwest flights havana
Photo: gildemax

This one sometimes gets up to around $99, but typically hovers around $59 to $69. 

If getting to Cuba is on your bucket list, get thyself to Tampa first!


To Sum It Up

There are certain city pairs that are regularly cheap on Southwest.  They include:

  • Columbus and Cincinnati to Washington, D.C.
  • Atlanta to Nashville
  • Louisville to Chicago
  • Ft. Lauderdale to Grand Cayman
  • St. Louis to Atlanta
  • Anywhere in California to anywhere else in California
  • Tampa to Havana

Which cheap Southwest flights have you found to be consistent?

[mv_video doNotAutoplayNorOptimizePlacement=”false” doNotOptimizePlacement=”false” jsonLd=”true” key=”p3oqltrscxywjdwr2udh” ratio=”16:9″ thumbnail=”” title=”How to Change a Southwest Flight” volume=”70″]