8 Ways to Stretch Your Southwest Points as Far as Possible

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Lyn writes about Southwest Airlines on GotoTravelGal.com and offers a free guide on how to earn the Southwest Companion Pass, which Emily and I believe is the best deal in travel.  I’ve asked her to share her tips on how to make your Southwest points go as far as possible.

Lyn:   One of the best parts of collecting and redeeming Southwest points is the ability to book any flight any time with no blackout dates.  

Unlike other frequent flyer programs, which release limited award seats and charge a set number of miles or points per flight, Southwest’s program sets the points required to book an award flight based on the current fare price.

8 Ways To Stretch Your Southwest Points As Far As Possible

My Family of 4 Visited 6 Destinations Within 1 Year, Including the Rocky Mountains, by Stretching Our Southwest Points!

I’ll show you how to make the best use of Southwest points by taking advantage of these awesome benefits.

How to Make the Best Use of Southwest Points

By following these methods, my family of 4 was able to travel to 6 destinations within the span of a year for less than $100 per flight for all of us.  You can do it, too!

1.   Earn the Southwest Companion Pass

The first – and most important – step to saving as many points as possible is to earn the Southwest Companion Pass.  The Southwest Companion Pass lets 1 person fly free with you from the time you earn the pass until the end of the following year.  That means you do not have to incur any cost or use any points for this person’s ticket, except for taxes and fees.  That is a TREMENDOUS SAVINGS!

8 Ways To Stretch Your Southwest Points As Far As Possible

It’s Easy to Earn the Southwest Companion Pass, Which Saves the Cost in Cash or Points of 1 Person’s Flight

That meant that 1 of my family members always flew nearly free.  In my case, we chose my husband as my companion, since he was the most likely person to always be traveling with me.  

But if you find you need to switch companions, you can make a change up to 3 times in 1 year AFTER initially designating your companion.

You can easily earn the Southwest Companion Pass by signing-up for 2 Southwest credit cards when they have 50,000 to 60,000 point bonuses.  You can download my free guide, “The Step-by-Step Guide to Earning Your Southwest Companion Pass” for complete details.

2.   Book During a Sale

Southwest has A LOT of sales.  So you’ll want to make sure you are booking your ticket while they are having a sale.  Not all Southwest sales are equal, but it’s better to buy during a sale than not.

Because Southwest bases the points price of a flight on the fare price, the points required to book a ticket decrease during sales – just like the cash price.  To spend as few points as possible, ALWAYS BOOK DURING A SALE if you can!

8 Ways To Stretch Your Southwest Points As Far As Possible

Try to Only Book Southwest Fights During Their Many Sales

But, even if you book during a sale, that DOES NOT mean you got the best deal.  Make a note of the points you redeemed for your flight and then continue to check the price to see if it drops.  

If it does, you can cancel your existing flight with no penalty and re-book the flight at the better rate.  As soon as you cancel a flight paid with points, the points immediately go back back to your Southwest account.  So you can use them to book a different flight.

3.   Don’t Book Flights in the Summer

Summer tends to have the highest ticket prices.  So it’s not a great time to book flights unless you have to.  

If you want to save, fall, especially the months of October and November, as well as January will likely be your best bet for the lowest cost flights.  In 2016, however, Southwest offered 1 of its best sales of the year in early June, so always keep an eye out and check prices.

Also, Southwest only releases bookings about 6 months ahead, so you’re limited in how far you can book a flight.  But a good plan would be to have points in place by fall ready to book your winter and spring travel, book summer in early spring, and book fall in early summer.

4.   Book Tuesday or Wednesday Flights

In general, the cost – and therefore, the points price – of Southwest flights are lower if you travel on Tuesdays and Wednesdays.  We almost always fly on Tuesdays, which is difficult when considering school schedules.

We think it’s worth the lower fare, however, for our kids to miss a couple days of school.  Think of the travel they are getting in return!  Of course, that’s up to your judgement and your family’s individual situation.

8 Ways To Stretch Your Southwest Points As Far As Possible

Usually, Tuesdays Have the Lowest Priced Flights in Both Cash and Points

Tuesdays are actually a great day to fly, because there are fewer people traveling (thus the lower cost).  And so security and check-in lines are shorter, making it a more pleasant experience.  So, if you can fly on a Tuesday or Wednesday AND use fewer points, definitely do it!

5.   Be Willing to Connect

Flights with connections between your departure and destination city also tend to cost less.  If you’re willing to get off the plane in Atlanta, Chicago, Denver, or another connecting city, you’re going to pay fewer points.  But check and make sure there aren’t non-stop options with the same or similar point prices  you never know!

6.   Fly at Off Times

Do you mind a 5:40 am flight?  If not, you can save a bundle in points!

I took a 5:00 am flight to New York City recently and loved the fact that I got to see the sun rise over Manhattan and arrive to my 1st appointment by 9:30 am in the city.  Pretty amazing!

8 Ways To Stretch Your Southwest Points As Far As Possible

I Actually Really Enjoyed My 5:00 am Fight to New York City, Because I Got to See the Sun Rise Over Manhattan and I Saved on Points

Alternately, flights that arrive in the wee hours of the morning past midnight are also likely to be fewer points.  Night owls can definitely take advantage of savings by choosing late night flights!

7.   Book Off Season and When School Is in Session

I hate to tell you, but everyone flies to Florida over Spring Break and to Denver over Christmas break.

So you’re not likely to score a good deal when booking during a destination’s peak season.  Try to wait until a time of year that is less popular to visit a destination.  My family loves to visit Colorado in the summer, for example, to take advantage of hiking and other outdoor activities.  And flights to the area are typically much more reasonable in summer than winter months.

8 Ways To Stretch Your Southwest Points As Far As Possible

The More You Can Fly When School Is in Session, the More Likely You Are to Save Versus Traveling During Vacation Seasons for Families With School-Age Kids

Keep in mind school schedules, as well, because fall break, winter break, spring break, and, of course, summer are heavily traveled months when families are able to vacation.  The more people booking flights, the more expensive and more points you are likely to spend.

8.   Choose Cities with Low Fares From Your Destination

One of the best ways we maximized our Southwest points was to choose destinations that were already reasonably priced from our home city of Indianapolis.

Over the course of a year, we flew to Orange County (twice), Orlando, Ft. Myers, Denver, and New York City.  New York City, for example, was 1 of the best deals and cost less than 7,500 points round-trip for each of us, meaning all 4 of us flew for ~21,000 (remember, 1 person required no extra points due to the Southwest Companion Pass).

8 Ways To Stretch Your Southwest Points As Far As Possible

We Flew to New York City for ~21,000 Southwest Points – a Great Deal That Helped Stretch Our Points

If we had instead chosen to fly to Mexico or the Caribbean, we could have easily blown all our points in 1 trip, which of course is an option.  

By choosing destinations that are usually the lowest cost options from your home airport, however, you can extend your travels to multiple places, depending on how many people are traveling with you.

Bottom Line

You can really stretch your Southwest points far, even for a family of 4 or more!

My tricks include:

  • Earning the Southwest Companion Pass
  • Watching for sales
  • Booking flights during off seasons
  • Early morning or late night times
  • Flying on Tuesdays and Wednesdays
  • Making reservations at the right time of year
  • Opting for connecting flights
  • Choosing traditionally low-cost destinations

Try them!  You’ll be amazed at how far your points will take you. 🙂

How many places do you want to visit this year with your Southwest points?

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6 responses to “8 Ways to Stretch Your Southwest Points as Far as Possible

  1. Also, you could mention that once booked and you see a sale, you can always call and ask them to give you back the points. I did that on a trip book from Indy to IAD and had 3,000 points returned to my account–the cost of one of the flights!

    • I always book one way flights on Southwest. It doesn’t cost any more than a roundtrip ticket. If the number of points required falls, I’ll cancel and rebook the flight at the lower rate and the extra points just go back to my Rapid Rewards account. You can’t do that trick with roundtrip tickets because if you cancel one leg, the other leg gets canceled too.

  2. For three years running the biggest fare sale has been in June, the first Tuesday in June. It is not the one with $39 fares, it starts at $49 but it is the one with the sales to the most destinations. However, so far this year does not compare favorably to last year, at all. I look at the same city pairs often, and by this time last year I had booked a couple of trips during really good sales. The fare sales so far, have not included any where near the same savings.

  3. If we’ve earned the southwest card bonus points in the past but then cancelled the card… are we able to apply for the card again and earn the bonus points again after a certain period of time?

  4. If I change my companion 3 times in the first year, can I change my companion 3 more times during the second year (if I receive my CP early in the year)?

  5. My wife and I both have earned Southwest Airlines points – I have the Companion Pass but she does not. As long as we fly together, we are able to to get more flights by her buying me a ticket with her points and I buy her a free ticket by using my Companion Pass. So it is like both of us having the Companion Pass – one of us flies free on every trip.