5 Tips for How to Tell When a Southwest Sale Is Worthwhile

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Lyn blogs about Southwest at GotoTravelGal.com and has a free guide, “The Step-by-Step Guide to Earning the Southwest Companion Pass,” to help folks who want to earn what Emily and I believe is the best deal in travel, the Southwest Companion Pass.  

Because she follows Southwest so closely, I’ve asked her to share her advice on how to know which Southwest sales are good and which aren’t, because Southwest has a lot of them!

Lyn:   It seems Southwest has a sale at least every other week, but is it really a sale and are the fares really a good price?  It can be hard to tell!  

I watch Southwest almost daily, so I’ve developed a keen eye in determining what is and what isn’t good pricing.

5 Tips For How To Tell When A Southwest Sale Is Worthwhile

Is This a Good Sale or a Bad Sale? Read on for Tips to Figure It Out!

I’ll share strategies for picking the best Southwest fare sales!

Which Southwest Sales Are a Good Deal?

Link:   Southwest

Link:   Southwest Fare Sales

Here are my top tips to help you determine if a Southwest sale is worth using those valuable Southwest points and your hard-earned money.  Or not. 🙂

1.   Research Fares From Your Destination Over Time

The best way to know if a Southwest sale holds muster is to have an idea of what really is a good price from your home airport to destinations you frequent or that are on your wish list.

5 Tips For How To Tell When A Southwest Sale Is Worthwhile

Check the Low Fare Calendar Regularly to Learn the Lowest Points and Cash Prices for Your Favorite Routes

Check at least monthly to see what the going “points” price and “cash” price is for these cities using the Southwest Low Fare Calendar.  The calendar will show you the lowest fares over month period.  

Over time, you’ll get a feel for what the rock bottom prices are for your top destinations, and you’ll be able to tell if Southwest is offering you a true steal or just more of the same.

2.   Pricing of Less Than ~$79 for Longer Flights

While Southwest sales often have really low prices for flights between cities in close proximity, such as from Indianapolis to Chicago or from Dallas to Houston, that’s not necessarily an indicator of a good deal.  These flights are most always pretty cheap.

5 Tips For How To Tell When A Southwest Sale Is Worthwhile

Fares of Less Than $79 or ~4,000 Southwest Points One-Way Indicate a Good Sale

Instead, keep your eye on the flights that are for longer distances and not just the next city over.  Can you find a fare price less than $79 or 4,000 points one-way to a destination where you’d like to fly?  That’s usually a good deal.  

From Indianapolis, for example, which is my home airport, we can typically find prices below $59 or 3,500 Southwest points to New York City and Washington, DC, during a good sale.  When I see prices for those cities hit that mark, I know I’m likely looking at a decent sale.

To find the prices for a sale, click on the sale advertising on the Southwest fare sale page, then choose your departure city from the drop-down box to see the advertised fares.

5 Tips For How To Tell When A Southwest Sale Is Worthwhile

Choose Your Departure City From the Drop-Down Box on the Sale Page to See Advertised Fares

Note:   If your area is served by more than one airport, be sure to check fares for each airport separately.  For example, New York (Newark and JFK) or Washington, DC (Dulles or National).

3.   Check the Dates of Travel

Some Southwest sales are only for specific dates of travel, such as the winter holidays, weekend, spring or summer.  Be sure you check the sale details to see which flight dates are covered, so you’re not trying to book a summer ticket during a spring sale.

5 Tips For How To Tell When A Southwest Sale Is Worthwhile

Check to See What Dates of Travel Are Included in the Southwest Sale

And scroll down to the bottom of the fare sale page to see blackout dates or day of the week restrictions.  For example, many Southwest sales exclude travel on Fridays and Sundays, which makes it tricky to plan a cheap weekend getaway!

4.   Look for TV Ads

One of the hallmarks of a big Southwest sale is that they will shell out some big bucks for major television advertising.

5 Tips For How To Tell When A Southwest Sale Is Worthwhile

If You Start Seeing Southwest TV Commercials, There’s a Good Chance They’re Having a Great Sale

Last year around the Super Bowl, there were Southwest commercials aplenty advertising a “major sale.”  If you start to see Southwest ads show up during your favorite sporting events and TV shows, zip on over to Southwest.com and see what deals you can find.

5.   Time of Year

There are certain times of year that tend to lend themselves to good Southwest sales.  In 2015, I found the best deals in November and December for 2016 travel.  Last year, Southwest had a good sale in early June with some surprisingly low fares, and this year, January and February have proven to have some good prices.

Hopper, a mobile app that predicts and analyzes airfare, says that average airfares for all airlines tend to hit their lowest in October and January.  Summer is typically the worst time to book travel, offering the fewest sales.

5 Tips For How To Tell When A Southwest Sale Is Worthwhile

Planning a Winter Getaway to the Tropics? You’ll Likely Find the Cheapest Fares in October and January

My advice is to book your flights as early as you can, knowing that with Southwest you can always cancel and re-book with no penalty.  Keep in mind that if you pay with cash,  Southwest will only issue you a travel credit, good for 1 year, versus fully reimbursing you.

If you book with points, your Southwest points are credited right back to your Southwest Rapid Rewards account, another perk of booking with points!

Even if the sale is not the best one you’ve ever seen, it’s always better to book during a sale than when there’s no sale going on.  Prices may not be at their lowest, but they will be lower than on non-sale days.  Again, you can always book the flight, knowing you can cancel or change with no penalty should a better deal emerge.

Bottom Line  

Southwest runs a lot of sales!  And they’re NOT always the best deal.

To determine if you should book flights during a Southwest sale:

  • Do your research ahead of time to get a feel for good pricing to your destinations
  • Keep an eye out for longer flights priced at ~$79 or less
  • Consider the time of year and whether your travel dates or days of the week are included
  • Look out for good sales in October and January, the months where airfare is typically lowest
  • Watch for TV ads, which are a good indication of a better sale

Even if you don’t have firm plans, or aren’t sure it’s the best deal, you can book anyway and change or cancel your flight later without penalty if the fare drops or you change your mind.

Let me know if you have other strategies for finding the cheapest Southwest flights!

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7 responses to “5 Tips for How to Tell When a Southwest Sale Is Worthwhile

  1. I booked 4 award tix one way for 2,880 points. The fare dropped to 2,000 points per person for 4 people. When I go into my flight itinerary and click “change”, so I can rebook at the New points total, I goes up to 5,800 points per person. Why is that? Again, an independent search for 4 people come back at 2,000 points. Do I need to cancel altogether? Why can’t I just change the itinerary to same flight and bank the difference in miles?

    • Usually it means there are not enough number of tickets available for those points. for instance may be there are only 2 tickets available for 2000 points per person and not 4 tickets for those points. If thats not true then you can try one of these 2 options,
      1. Assuming you have enough points to book new set of tickets without having to cancel the existing one then first book the new tickets before canceling the existing itinerary. (or)
      2. You can call up customer care, they can book for those points on your behalf.
      Hope this helps.

  2. In first week of Jan, I booked FLL SJU return for 3,456 points per person, for the president’s day week. Used companion pass too.
    Flying this Saturday, total cost for family of 4 -> 10,368 points + $44.80.

  3. I just received the Companion Pass and booked 1 ticket (plus companion) from LAX-BNA-MSY-LAX. for 50,140 miles plus $33.60. I was OK with this until I read this article. I started thinking I didn’t get much of a deal. I hadn’t read the fine print about the cheaper prices being midweek. Our 15 night trip is all on points, and I had difficulty getting the hotels I wanted in New Orleans. I really had to adjust the trip to find point availability. I also booked one night in Louisiana using IHG point breaks and that was tough to find availability. I would have delayed this trip until later in the year, but we have a new credit card we need to make minimum spend on by early in April, and the trip certainly helps with that. It gets a little tougher trying to find the best prices, good flight times with a minimum amount of stops, and “point” hotel availability. I guess I should just be happy that I got the whole trip booked on points, and try to do better Rapid Rewards- wise next time.

  4. I’m looking to go from Chicago to Denver in the summer. It seems the point values for that trip don’t usually drop below 10,000 each way. Not great but hot time of year to go to Denver I suppose.

    • The high price is more likely attributable to the fact that it’s simply 4+ months away. Southwest charges a lot for those flights. See what the best days and times to travel are in the next 6 weeks, and book a flight in the summer for that day and time. Meaning, if you see that Friday morning 8:30am flights are cheap in March, they will likely also become cheap in July. Book it now using miles and rebook as the price falls. You gotta have cahones!

  5. We travel from Milwaukee to Orlando every July. Last year we purchased tickets on Southwest on New Year’s Eve for $98 each way. This year – we’re into March and the lowest fares are $160/$170 each way. I keep watching for a sale, but the only sales are for Spring and now Fall travel. Aren’t there going to be any sale fares for the summer?