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Be Aware of These Quirks when Rebooking Southwest Flights

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:

  1. 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.
  2. 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. 
  3. 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.
  4. 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.
  5. 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.

Bottom line

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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Author: Leana

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.

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23 thoughts on “Be Aware of These Quirks when Rebooking Southwest Flights

  1. Thanks for the mention, and (as always) the helpful post! I would say, however, that frequent checks of the prices probably added up to more than 15 minutes of work in the end. I just wanted to add that because there are so many little tips and tricks that at first glance seem like no-brainers, but either in actual practice or just all together end up being WAY bigger time sucks than I counted on.:)

    • @Audrey Absolutely!!! So right you are, my friend. It took me less than 15 minutes to rebook this reservation but of course, I didn’t count all the time I spent tracking the flights over the last few months.
      That’s the thing about this hobby. Unless you are an anal-retentive, OCD-leaning person, it will drive you bananas. That’s why a tiny subset of population bothers with miles and points. To us it seems like everyone is doing it but alas, that’s not the case at all. You have to enjoy digging through fine print and checking stuff repeatedly, otherwise the juice won’t be worth the squeeze.

  2. We have never flown Southwest, but may need to for a few trips in the near future. How do you get assigned seating especially since you have children? I don’t want to be away from my children on a plane especially in case of an emergency.

    • @Stephanie You may want to read Nancy’s post that has a section on this topic: https://milesforfamily.com/2016/12/02/parents-dont-afraid-fly-southwest-airlines-kids/
      When your kids are 6 and under, you’ll get Family Boarding, which is right after A group. This will allow you to make sure that you get seats together.
      If you have older kids, make sure to check in right at 24 hours before the flight. I honestly don’t think it’s an issue 99% of the time. Most passengers will switch seats with you if you have a kid. Only few will make a stink. I believe Southwest will also allow you to buy Priority Boarding, though I’ve never done it.

    • @Stephanie my family has never been separated on a Southwest flight, and we don’t pay for the Early Bird boarding. We just board during family boarding, and have never had a problem. I believe this summer a new law will take effect that requires airlines to sit kids 13 and under next to a parent. I’m curious to see how that is put into practice on various airlines.

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  4. I just successfully added a night to our upcoming Hyatt Ziva Cancun trip by finding a southwest flight a day earlier and 2.000 pet cheaper. There is a ton of availability to Cancun right now at about 4200 SW points. I’m loving southwest more and more. Definitely keep checking, I have found that I eventually find cheaper tickets for the same or
    Better itinerary on about half my southwest flights.

    • @Cheapblackdad Nice! That’s a very cheap price for a flight to Cancun. I absolutely love Southwest. I just hope they eventually add Hawaii. Right now economy flights overseas are so cheap, it almost doesn’t make sense to use miles. Domestically, however, the prices are mostly holding steady. That’s why dirt cheap Southwest fares are always welcome in my house!

    • Leana,
      I owe this trip to you and your readers. We were gonna use them in Chicago or Boston once we pushed out our Hawaii trip. But you and Stephanie I believe said we should Check the Hyatt Zs. Well actually save money on this trip as we won’t spend on food for a week, or spend money on gas for our cars, or power for our home. And the southwest flights totaled less then 20k its round trip for both of us. As in total.

      And, while I’m not a Trump fan, that dollar peso exchange rate, tho.

      • @Cheapblackdad I’m very happy for you! I think this is a perfect way to use the certs. Enjoy this trip with your wife! Relax and take some pictures, I want to see them when you get back.

    • @KKnur I could have sworn that I saw it listed in this guide https://cdn.f9client.com/api3/file/1130204/inline/SapphirePreferred_Visa_Signature_V0000037_BGC10374_Eng_P.pdf?__gda__=exp=1488392245~acl=/api3/file/1130204/inline/SapphirePreferred_Visa_Signature_V0000037_BGC10374_Eng_P.pdf*~hmac=e9471f1ccba09190f4a8bc5b983ddad23147927922f6915d56d9eb74cf73de8e
      However, I looked and can’t find it now. I have seen reports that some cardholders had a hard time making a claim without having a roundtrip ticket, but perhaps it was due to rep’s incompetence. Usually, having two one-way tickets will be sufficient, I just wanted to caution readers. I’m leery of any travel insurance attached to a credit card and prefer to purchase a standalone policy. Perhaps I’m just paranoid.

      • There is a requirement that the trip be 60 days or less. So perhaps the insurance company is interpreting that as needing proof of a return/roundtrip ticket? (I am interested in trying to find those reports.) So the downside I see for booking a roundtrip on SW is not being able to make changes to the return flight once the trip has already started. Is there another one of which you are aware? Thanks for the initial reply!

      • 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.

        P. 16 of CSP benefits guide. CTRL+F for “round-trip”.

      • @Thegazelle Yup, there it is. Thank you for pointing it out. I’m dealing with some health issues right now, so my brain isn’t functioning at 100% capacity.
        I honestly believe booking two one-way tickets will probably satisfy the requirement, but it is a concern. Chase could try to weasel out of paying out on the policy. Personally, I like to get my own travel insurance anyway. I’ve seen too many problems when folks rely on credit cards for protection. But for relatively cheap trips, it’s probably fine.

    • @KKnur I saw several comments on travel blogs, but can’t remember which sites they were. It was probably just a Chase rep who didn’t know what they were doing.
      I recommend you reach out to Chase if you are concerned. Honestly, I’m not seeing anything about round-trip requirement, so I’m pretty certain it would be fine. Personally, I book one-ways regardless, but I also usually purchase my own insurance policy, so it’s not a huge concern. To me, the flexibility of having one-way ticket outweighs any potential drawbacks. Well, unless there is a huge cancellation penalty involved. In that case, I may reconsider.

  5. 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.

    • @Weedibix Very interesting and helpful comment! I never had a CP, so I didn’t realize there is special drill involved. Hmm, yeah, that does sound more labor intensive. I will update the post with your comment. Thanks!

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