When I booked my Southwest flight to Jamaica last year, I thought I was getting a fantastic deal. Even though international taxes to Caribbean islands are crazy high, paying just 4,600 Rapid Rewards points one-way is dirt cheap. Of course, since then my reader Audrey has pointed out that Jet Blue might have been a better choice, and I agreed.
Well, being the OCD person that I am, over the last few months I kept diligently checking my Southwest flights to see if a cheaper price would pop up. After all, you can rebook with no penalty. No dice. March is a high season in Caribbean, so I pretty much gave up. And I definitely didn’t think I would find a good deal just few weeks before the trip. Wrong!
While the outbound flight went up in price, the flight from Jamaica to Orlando got cheaper. I found it for only 2,660 points per person. As a result, I saved close to 8,000 points total for only 15 minutes of work. This is why it’s better to book Southwest flights as one-ways rather than roundtrip. It makes it much easier to cancel or rebook.
That really goes for many award redemptions, except those that have high cancellation penalty. That’s because you will have to pay it twice if you book one-ways. Also, if you are relying on travel protection via cards like Chase Sapphire Preferred, you are required to have a roundtrip ticket in order for your benefits to kick in.
Update: My reader KKnur has mentioned that roundtrip requirement is not listed in the benefits guide. In response, reader TheGazelle pointed out this definition on page 16 of CSP benefits guide: “A Covered Trip is a period of round-trip travel that doesn’t exceed three hundred and sixty- five (365) days away from your residence to a destination other than your city of residence.” But as a general rule, Avios (British Airways program) and Southwest award tickets should always be booked as one-ways.
Rebooking process on Southwest
If you are rebooking flights at the lower price, you don’t have to cancel them first. You can just hit the “change” button, and it will give you the option to search for a new flight. Update! Southwest has changed the terms and now, if you change the reservation, it will become non-refundable. Here is how you can access your reservation:
You can book the same exact flight at the lower price with an automatic points refund/adjustment. When you get to the screen to review your changes, you can see the price of your old ticket compared to your new ticket and the amount of points that will be refunded. The default is to use the travel funds from your original booking, so you don’t have to input anything.
My reader Weedibix added the following helpful tip if you booked while using a Companion Pass:
“About checking for lower prices & rebooking with a companion flight:
If you have a companion pass, and your companion is on the flight, the system will not allow a change until you first cancel the companion flight.
So the drill is different. First, compare the price, or price in points that you paid to the current, hopefully sale price.
You have diligently kept a record of the price you paid, and updated it each time you rebooked, right?
You can compare by starting a new booking for the flight you want, and getting yourself to the purchase page. This will show the current price, or price in points.
If it is significantly lower than the one you paid, cancel the companion booking, then go through the change process Leana describes above, then add the companion. (You may have to wait 5-10 minutes before the system allows the new companion booking.)
Remember to use the refund to pay the taxes, so that you do not have to track it.
Note: this means that there is a possibility that the flight is now sold out, and you will not be able to rebook the companion. This has never happened to me, and it seems quite unlikely, but it theoretically could happen.
Comment: You can see that this takes some time. So my practice is not to check companion fares frequently, but only when I learn of a fare sale, to increase the probability that the process will be worth doing. Also, as the flight date gets closer, prices tend to rise, so it becomes very unlikely that you will get a lower one. I would not take the time to check if the flight date is within 4 weeks.”
If you are not sure when you will be using the funds and just need to cancel the flights for now, the process is a bit different. You will need to log in to your account, find the reservation and cancel it. Depending on a flight, you will be given an option of refund of your taxes or having that amount held in a travel fund.
Obviously, you will want to select the former if at all possible. Unfortunately, since I paid my taxes with a Southwest gift card, I didn’t have a choice. My funds will expire in October of this year, so it’s “use it or lose it” kind of thing. Take a note of your reservation number, you will need it for your future flight.
OK, your reservation is cancelled and few months down the road you are ready to book your new flights. When you get to your payment options, here is where you’ll need to put in the old confirmation number:
You will have to put the name of the first passenger listed on the old reservation. You won’t need to do this separately for all the other travelers. The system will automatically apply the funds if the names are identical. If there is a difference in the amount of award taxes, you will have to pay it separately. I was presented with the bill of 80 cents. You can pay it via Southwest gift card (next to “travel funds”), PayPal or a credit card.
Flying a family of four from Jamaica to Orlando for only 10,000 points total (plus exorbitant taxes)
Southwest LUV vouchers work a bit differently because you can’t use them towards taxes or fees. I’ve heard of people using them to book flights and then canceling the reservation immediately afterwards. Reportedly, you can then use them as travel funds. I can’t vouch for this strategy, plus, it’s a rather sketchy maneuver. You will have to decide on this one. LUV vouchers are usually given out to customers when there is a problem with a flight or reservation.
Few tips for booking Southwest flights:
- If you have four people, put in two people on the reservation and see what kind of price pops up. Southwest allots only so many tickets in the lowest bracket. Once it fills up, the rate goes up as well. We actually ended up booking our tickets from Orlando to Jamaica in pairs for that reason. I paid 4,300 points per person for me and daughter, and my husband’s and son’s tickets ended up costing 6,000 points apiece.
- If you are not ready to rebook your reservation, make sure to print your old confirmation page or write down the details. You will need them for your new tickets. Make sure to take note of funds’ expiration date. Be aware, the date indicates NOT the deadline by which you have to book your reservation, but rather the time you have to take your flight.
- If you have a card like Chase Sapphire Reserve or Citi Prestige, you can use your annual travel allowance to offset the taxes or ticket price. This will also give you access to travel insurance since at least a portion of your flight is paid for with a credit card. Be aware, if you buy Southwest gift cards and use them to pay taxes, you will not get this coverage.
- Make it a habit to check the price every few days. You never know if a crazy cheap sale will pop up for your destination.
- Follow a frequent flyer miles blog (like this one) and sign up for Click N Save alerts so you can be the first one to know about special deals and new routes. BTW, Southwest schedule is now extended through September 29th (h/t MMS).
Ways you can accumulate Southwest Rapid Rewards
Southwest is a transfer partner of Chase Ultimate Rewards. Your best card choices are: Chase Sapphire Reserve (apply in branch in order to get 100K points if you are under 5/24), Chase Ink Business Preferred or Chase Sapphire Preferred. These offers are subject to 5/24 rule. You can use Ultimate Rewards points from the sign-up bonus to transfer to Southwest program on 1:1 basis.
Chase also issues two personal Southwest Rapid Rewards cards that currently have 50k bonus points after spending $2000 in the first three months (and a business version that offers 60K points). All are subject to 5/24 rule.
The Plus version of the card (pays us commission) has a $69 annual fee, and the Premier version has a $99 annual fee. You can use my personal referral link if you want to apply for the latter. Thanks if you choose to do so! Having a co-branded Southwest credit card allows you to redeem Rapid Rewards points on gift cards to places like Walmart and Target.
Don’t forget that you have till March 31st to redeem your Marriott and SPG points for travel package and having them qualify for Companion Pass.
It’s no secret that I’m a huge fan of Southwest frequent flyer program. The fact that you can rebook your flights with no penalty is a big plus for families who are looking to stretch their precious Rapid Rewards points. Add to it free bags and ability to redeem points on gift cards (if you have a co-branded card), and it’s easy to see why this program is a winner for regular folks like me. Most importantly, many routes can be dirt cheap if you are willing to keep track of price changes.
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Leana is the owner and founder of Miles For Family. She enjoys beach vacations and visiting her family in Europe. Originally from Belarus, Leana resides in central Florida with her husband and two children.