93. Buckle Up, BOGO: Strategies for Maximizing the Southwest Companion Pass with Dr. Michelle Walther

Welcome to Point Me to First Class, the only show for employed professionals, entrepreneurs, and business owners who are looking to optimize their higher-than-average expenses to travel the world. I'm your host, Devon Gimbel, and I believe that your expenses are your greatest untapped asset if you know how to leverage them. Ready to dive into the world of credit card points and miles so you can travel more, travel better, and travel often? Let's get started.

Devon: Welcome back to the podcast, everybody. Today, I am excited to be joined by Dr. Michelle Walther. Michelle is an emergency medicine physician, mom to two amazing girls, and wife to a retired Army medic. When she's not saving lives, she's saving miles, turning her love for travel into a family adventure fueled by points and miles.

It all started back in 2007 when she opened her first Southwest Rapid Rewards card, and since then she's been flying high, sharing the world with her family, and making memories on one-on-one trips with each of her kids. Michelle is a huge fan of the Southwest Companion Pass, and she is here today to share how she's leveraged what's been called the best deal in domestic travel to save money and build travel memories with her family. 

Now, for any of you who have been eyeing the Southwest Companion Pass and might be wondering whether you should go for it, now that it's the perfect time of year to put a Companion Pass plan into place, Michelle is here to give you real examples of the value that she's gotten from the Companion Pass and share tips on how you can do the same. Michelle, welcome to the podcast, and thank you so much for joining me today.

Michelle: Of course. I'm so happy to be here. Thank you so much for having me.

Devon: Absolutely. So, we are going to dive into all things Southwest Companion Pass, but can you kick us off and tell us how long have you held a Companion Pass? When did you first qualify for one of these, and why do you make an effort to achieve a Companion Pass? 

Michelle: My oldest daughter is nine, and I have had a Companion Pass probably for five years. I did a whole lot of traveling with her when she was little and a free lap child. My husband was gone, deployed, training all over the place. So the option was to sit at home with my one child and do nothing or to go travel. 

So, she and I traveled all over the place while she was a free lap child, and I was like how can I make this keep working? So, that's when I really started trying to achieve the Companion Pass, and I managed to do it organically without churning cards a few times before I really knew that you could do that. 

So, the first few years, I just charged all of my income taxes because I'm a contractor, nothing gets taken out of my check, and I made Companion Pass that way. I earned it the first few times, saw how amazing it was, and said, okay, this is something I definitely want to keep and have tried to maximize it all the years that I've had it since.

Devon: So, for the Companion Pass that you are holding right now, I'm curious, when did you qualify for it? Are you on like year number one or year number two of your current Companion Pass? 

Michelle: I'm currently on year number two of my Companion Pass. I actually last year qualified organically by spend, and then I had, I think, two referrals that put me over the edge. So I didn't have to open any cards. So, I had it last year, but then I just kind of requalified organically, and I've done that again this year. 

So I haven't had to open cards again, which is great for me because my Southwest card is my oldest credit card, and it's always like oh, am I going to open two new business cards? Do I cancel my oldest credit card, which I still have not done? So, for me, it's worked out to get referrals and put some organic spend on there. But my upcoming plan was to open two business cards in January, and now I've gotten several referrals. So that plan is on hold until next year again.

Devon: I think this is a great time to kind of dig into different strategies for achieving the Southwest Companion Pass because I think certainly for most people kind of the easiest path towards earning a Southwest Companion Pass, as you kind of alluded to, is to plan and strategize on earning the welcome bonuses on two separate Southwest credit cards. 

So, since right now there's a rule in place where one individual cannot hold more than one of the personal Southwest credit cards issued by Chase, usually that looks like a combination of one personal Southwest credit card and one business Southwest credit card, or earning the new welcome bonus on two of the business Southwest credit cards. So, all of these are issued by Chase.

I'm really curious to hear from you, as someone who is very well aware of that strategy but has actually been earning their Companion Pass through organic spend and referral bonuses, do you do an analysis kind of at the beginning of whatever your cycle is for getting approved for a Companion Pass and really kind of break down what is your break-even point that helps you decide whether or not you're going to favor using organic spend to earn a Companion Pass or whether or not you actually do want to open up credit cards? Could you walk us through that process at all?

Michelle: Early on, I wasn't doing any analysis. I was like, I think I can make this work. I think it'll be beneficial for the family. I want to earn something on these tax payments. So, I didn't really do any analysis. The past couple years, ever since I got involved in listening to your podcast and involved in the group and like super into points and miles, I have been doing more analysis. Okay, is it worth it for the Companion Pass? Should I focus my spend on something else, other kinds of points? 

The break-even point for us is probably $750 to $1,000. If I'm spending more than $750 to $1,000 to get the Companion Pass, I'm not going to get enough out of it to really make it work. I think in the past, I've spent a maximum of $500 in fees on paying my taxes to get to the Companion Pass.

Devon: That makes a lot of sense because I think that there are a lot of folks who are looking for what is that kind of least effort path towards getting a Companion Pass. For people who don't want to sign up for new credit cards, who don't want to take the route of applying for either the one person on one business or the two business credit cards in order to earn the Companion Pass, I think it is great to remember that for people who do have organic spend, that allocating some or a lot of their organic spend specifically to these credit cards can help you achieve the Southwest Companion Pass on its own. 

So, since you've qualified for the Companion Pass, you've held it now for a while. Can you estimate how many flights do you think you've been able to take advantage of flying a companion for free? How much money do you think that you have saved using your Companion Pass? 

Michelle: I've run the numbers for the last two years. That's when I started really keeping track. I'd say I probably take 10 flights a year. So, 10 one-way flights a year, 8 to 10, that I can maximize taking my companion with me. Last year, I took, looks like 2023, I only took six flights and saved $1,200. Then in 2024, I had one, two, three, four, five, seven, eight flights and saved $1,400 by just having a Companion Pass. So, you know, I haven't looked back for the previous years, but they were on par, maybe a little bit less travel than that.

Devon: Yeah. Can you give us some examples of how you've actually used your Southwest Companion Pass for travel? Do you have any favorite destinations or trips that you can break down where you know exactly what it is you booked and what you saved using your Companion Pass? 

Michelle: Yeah. So, for example, in February of 2023, we love Disney, and it's easy for us to get to Disney World from Nashville. So, I took my youngest daughter. I like to travel with my children alone sometimes. My husband actually doesn't love to travel, which is like kind of hard to admit on a forum like this. But I do a lot of traveling one-on-one with my kids. It's great bonding. They have a great experience. One-on-one time is really good for us. 

So, in February of 2023, we flew roundtrip from Nashville to Orlando. I paid cash for my ticket and then used the Companion Pass for my daughter's. So, I paid a total of $500 for my round trip ticket. I don't know why it was so expensive because that's a lot for a Southwest ticket. $1,120 in taxes and fees for her ticket. $478 was the amount that I saved by not having to pay for her ticket. 

I could have done that with points either. That's also because the great thing about the Southwest Companion Pass is you can use it on any flight that you're taking, whether you pay with points or with cash. It's awesome. I have been trying to requalify for A-List. So, I've been trying to pay for my ticket and then use points for everyone else. I think I'm going to fall short this year. Short by just a little too much that it's not even worth it to do, like, one flight to get there just because a couple of flights got canceled. I had to take some other backups. But it's a sad day. It'll be okay.

Another example is, so, if we're going to fly international, Nashville doesn't have a ton of international options. We have British Air that flies to London. We're getting some more options that they've just announced. But right now, British Air is our only option. So, in March of 2024, I took my two kids and my mom to Italy. 

So, we positioned ourselves from Nashville to LaGuardia. I paid $106 for my ticket. That would have been 8,000 points. Plus $11.20 for my daughter's ticket. Saved that amount that I spent on mine for a free ticket for hers. Then when we flew home, we flew back into Chicago to ORD. Then Southwest, thankfully, does have a few flights from ORD but mostly, they fly to Midway in Chicago. We were able to get a ticket. I think, for some reason, I paid points for my ticket for that one. It was 7,200 points for me. No points for my daughter. So, saved 7,200 points there. Just paid the $560 for her to come home. 

Then, third example, we, in June of this year, I took both of my girls down to the Hyatt Regency Coconut Point just for a few day getaway water slides before we went back to school. I paid cash for my ticket. I used a Companion Pass. Then I used points for my other daughter's ticket. So, the round-trip ticket would have either been 17,358 points for my one daughter. Then I paid $330 for my round-trip ticket, and I paid $11.20 for my other daughter's ticket. So, saved $330 on that trip. 

Devon: Yeah, I think that's such a huge benefit of the Southwest Companion Pass is that, obviously, the more you fly, the more you take advantage of it, the more you can save money from it. You mentioned that one of the great aspects of the Companion Pass is that you, as the primary Companion Pass holder, you can book your flight either in cash or you can book your flight using Southwest Rapid Rewards points. Then your companion gets to fly for free. 

Curious to hear you talk a little bit about how do you determine whether or not you want to book your own ticket in cash versus points? Do you have a system for deciding that, or is it just a case-by-case basis? 

Michelle: So, I do have a system. This year, my system has been I'm going to pay cash or buy Southwest gift cards at Costco sort of situation for my own tickets and try and earn A-list. Because the real benefit of A-list is that you don't have to check yourself in, and you get an early boarding period. Now, there's lots of Southwest changes coming. 

So I don't even know what's going to happen. But I know I like to be early on the plane because we always travel carry-on and want our space for our carry-ons and don't want to sit in the middle seat. So, that was my strategy for this whole year was pay cash for my ticket, use a Companion Pass, and then pay points for whoever else. 

Now, the other awesome benefit of Southwest is you can cancel your booking up to, I think, 10 minutes before the flight leaves. So, I do sometimes use points for my own ticket and my kids' tickets if I'm booking like a backup flight. Like when we were coming back from Amsterdam, we had a really long connection at ORD, like six hours or something. 

But I still was afraid some disaster could happen. We might not make it back. I don't want to have to book a last-minute ticket the next morning. So, I had backup tickets booked for all of us the next morning out of ORD to Nashville. Once I knew that we had made it to Chicago, I just canceled the backup tickets. All the points went back into my account. 

If you book with cash, then you get a credit. It's still really easy to use the credits. But the refund of the points directly back into your account is super easy. So, when it's a flight that I don't think I'm actually going to take, I will book it with points for myself. 

Devon: That makes a lot of sense. I'm curious if you have any tips or tricks for finding deals or booking great-priced points flights on Southwest. 

Michelle: So, Southwest doesn't release their tickets like most airlines. They release them in batches, and it's not a full year out. I think right now you can book through August of 2024, and that just opened. Then I don't think they've announced the date yet. But in a couple of months, they'll probably open through, like, I don't know, November of, sorry, 2025. You can book through August of 2025 right now. 

So, if I know I have a trip coming up, which I plan pretty far out, just around school schedules and such, I try and book as soon as things drop if we know there's going to be a flight that we're going to go on. Knowing that when flights open up, they're not often the cheapest, Southwest has at least one sale a week. So, you may not be booking at the cheapest, but if you're booking with points, you can always go back, look at the cost of your ticket, and then just readjust it, and the points just automatically go back into your account. 

So, my tip is you're not always going to book it at the lowest price, but if you're diligent about going back to look, you'll get reduced fares. I recently flew to New York, and I paid something like $169 for a one-way ticket. It ended up, by the time we went, dropped to like $59 for a 6:00 a.m. flight to LaGuardia. Now, 6:00 a.m. is early, but I like cheap flights. So I'm willing to do it. So, you just have to be. Anytime I get an email from Southwest saying there's a sale, I go in and look at all my tickets. 

Now, I will say there's one annoying thing about having the Companion Pass, is that if you book your ticket and add your companion right away, then if you are trying to adjust your flight, change your flight, get points back, you have to cancel your companion, re-book your flight, and then re-book your companion. 

So, I have just now honestly stopped booking my companion until a week or two out when I'm sure that the price isn't going to drop anymore. Now, that almost backfired on me for our last trip because I looked, and I was like oh my gosh, I haven't added my companion, which is easy to do as long as the flight's not sold out. Thankfully, that flight was not sold out. 

Devon: I was actually just going to ask you, how often have you run into the scenario where you've gone to book your companion, their ticket, and the flight was totally sold out, or how often do you think that that actually becomes a risk? 

Michelle: I think it's very rare, and if it does happen, if you look and look and look and look, you can usually find a seat that opens because it can be any fare class. It can be the very expensive fare. As long as there's one seat open on the plane, so somebody's going to cancel in the last 24 to 48 hours, so you can usually snag that up if you look really hard.

I know I have a friend who travels a ton on Southwest, and she had forgotten to add her companion on a Christmas trip to Disney, and it was the day before, and she was like oh my gosh, I don't have a ticket for my son. But she looked and looked and looked, and she was able to get the ticket. Thankfully, I haven't actually forgotten yet. I've just come sort of close. 

Then, yeah, those are my big tips for how to use the Companion Pass. I will say, you know, Southwest is making lots of changes, and now they're going to be doing seat assignments, and they've said that your companion will also get a seat assignment if you have status. I'm not going to have status, it doesn't look like, so I guess that won't be a problem for me. But I could see that being frustrating if you have to add your companion when you book the flight, and then if you want to make changes, then your seat's already assigned, and you have to cancel and rebook. I don't know how that's going to look. I don't think anyone really does. 

Devon: Yeah, it'll be interesting to see how some of these changes that Southwest has announced are coming down the pipeline next year, potentially the year after, what impact they're actually going to have on the booking and the boarding and the flying experience, especially as it relates to things like status that I have. At least it seems like maybe actually getting shaken up a lot with some of those changes. 

So I guess the best thing to do is just kind of try to stay abreast of those, keep up with Southwest when they're making announcements, and just use the information they provide when they provide it to make the best decisions that we can. I'm curious to hear from you also, what have been some of your favorite destinations for flying Southwest using a Companion Pass, or are there any specific routes where you think having a Companion Pass comes in particularly handy?

Michelle: So as I mentioned, we go to Orlando with some moderate frequency. We really like Disney and Universal. So we have been back and forth to Orlando many times in the last few years. I said we weren't going this year and then we went for fall break. So sort of broke that. But last year, I think we went to Orlando four times, which was borderline too much. 

We have also used it for recent trips to Chicago. We went there just for a few days over the summer, stayed at the Higher Regency on points, had a blast. I have used it to visit relatives out in California. Really, it's great for anywhere you want to go.

The places that I haven't found great value out of it, just because tickets from Nashville are so expensive, is to go to the Caribbean and to Mexico and Costa Rica. Just from Nashville, we have a direct flight to Punta Cana on Southwest. But otherwise, there's like crazy layovers. They want you to have like stop in Orlando and then go to D.C. and sleep over and then get there. It doesn't make any sense for us to do. As I've gotten more into the points and miles game, I've realized there's other ways to get to those places for far fewer points. 

So with the more expensive flights, I've found that it's more beneficial for us to book, like via Alaska on American for 7,500 points and $5 rather than 30,000 points and a Companion Pass. I'm still saving points booking through that way. Now, I'm still a Southwest loyalist, but just for the international portion, at least from Nashville, it hasn't been great for us. Now, if you live in Orlando or Houston, I know they have more flights out of those places. It may be awesome for folks that live there, but I haven't found that benefit yet.

Devon: Yeah, that's a great reminder that just where you're based geographically may look different for you in terms of where some of the best deals or the best uses that you can get out of a particular airline, in this case, Southwest, and using their Companion Pass. 

So I want to go back to something that you were talking about a little bit before about mistakes that you have almost unintentionally made with your Southwest Companion Pass, intentionally waiting to add your companion, but then forgetting until close to your flight to actually add them. I'm curious if there are any other mistakes that you've made around your Companion Pass, or you've seen or heard other people making that we can be sure to try to avoid so that we can get the most value, the most use out of a Companion Pass as possible.

Michelle: So I think the biggest mistake people can make is going for that two card strategy and then signing up for a card about now in the year and meeting that spend before January 1st. Then you get the signup bonus in the year prior, and it's not going to count towards your Companion Pass for the next two years. So it's so important to be super aware of how much spend you're putting on the card, when you're putting that on the card, and when that signup bonus is going to hit. 

I haven't experienced this, but some people have said that there are rumors that Chase, you know, if you get close, like 50 to $100 away from that signup bonus, they'll just go ahead and give it to you, which is absolutely the last thing that you want to happen in when you're chasing the Companion Pass with two cards. So if you don't trust yourself to not follow it carefully, just don't open the cards until the end of December or early January. You're still going to get great benefit from nearly two years if you can meet those signup bonuses quickly. 

That's the biggest mistake. I can't really think of many others. Just forgetting to use it, forgetting that you have it would be a major bummer. But I use it so much that I would not forget. 

I think a lot of people who are new to this don't really understand the Companion Pass. You know, a lot of other airlines have what they call a Companion Pass where it's like Delta, you have a Companion Pass where you can use it on one ticket if you book it at the same time in this certain fare class and you're going this way. Or Alaska, I know you can book it maybe for half price. I don't know the details of the Alaska Companion Pass. 

But Southwest Companion Pass is truly nearly buy one, get one free for any flight you're taking for up to potentially two years if you time everything right. So for people who aren't paying attention, they're like oh, that doesn't make sense. Why would I want a Companion Pass? This is why you would want a Companion Pass because you get essentially BOGO flights for up to two years.

Devon: Yeah. I think that that is what distinguishes the Southwest Companion Pass so much from, like you mentioned, other airline programs that might offer a more kind of limited deal where you can get a discounted ticket or even a free companion fare. No one else offers anything like Southwest does where it's literally during your eligibility period. It's every single flight you can bring a companion and only have to pay the taxes and fees portion of their ticket. 

This actually segues really well into one of the last questions that I wanted to make sure to get your opinion on before we wrap up today. That is that especially this time of year where it is really common for people to make that decision about whether or not they want to put a plan in place to earn a Companion Pass. This is the best time of year to start thinking about how can you put yourself in a position to qualify for a Companion Pass as early in the following calendar year. 

So, in the case of where we are right now, as early in the 2025 calendar year as possible, it's really common for people to say okay, I see the value. I understand the value of the Southwest Companion Pass, but is it actually worth it for me? Do I fly enough to justify going after to Chase credit cards or putting a lot of organic spend on a Southwest credit card in order to earn this Companion Pass? 

While I don't think there's any hard and fast formula that we can just plug in that will spit out yes, it's worth it for you or no, it's not worth it for you. I'm curious to hear from you because I expect that probably a lot of your friends and family probably come to you and ask for your advice about whether they should get a Companion Pass. When do you think it's worth it for somebody to really make the effort to qualify for a Southwest Companion Pass? 

Michelle: First of all, I think really anyone who has Southwest that flies out of their airport could benefit from a Companion Pass. Even if you're just taking one or two trips a year, there's still a great savings there. So if you go for the two card strategy, you're going to be earning nearly 135,000 points or more by just opening those cards and getting those signup bonuses. So that's multiple free tickets for you plus a free companion on whatever flights you're booking for yourself and your companion. 

So if you think that you are going to take two trips in a year and you live at an airport that has Southwest, then I think that it's probably worth it for you, you know, at least to try and you'll probably get addicted like me and then never want to get rid of it. 

Devon: All right, Michelle, thank you so much for those tips. Thank you so much for that advice. I think it's going to come in handy for so many people. Now for folks who are wondering where they can learn more about you, more about what you do, where can they follow you or can they find you online? 

Michelle: So I have an Instagram where I post points and miles tips and my travels. You can find me there at Doctor Points and Passports. That's with the doctor spelled out and the and spelled out. Then I also have a website blog, Doctor Points and Passports dot com that I'm working hard to update. But, you know, life, kids, job, it's not as up to date as I'd love it to be. 

Devon: All right. Well, thank you so much for that. We will include both of those links in the episode description and the episode show notes so people can follow you more. Michelle, thank you so much for joining me today for teaching us all even more about the Southwest Companion Pass, how people can get great value out of it and the impact it's made for you in your travels. I appreciate your time so much. Thank you so much for joining me here today. 

Michelle: Thank you so, so much for having me. This is wonderful.

Thank you for joining me for this week's episode of Point Me to First Class. If you want more tips on turning your expenses into travel, visit pointmetofirstclass.com to learn more. See you next week.