Earn the Southwest Companion Pass in 2026
In this Hurdy Gurdy Travel Podcast episode, Justin sits down with Max Craig from Points to the Max to break down exactly how to earn and maximize the Southwest Companion Pass for 2026.
We cover the best timing for points, which cards to open (and when), stacking strategies, and what recent program tweaks mean for your plan.
Whether you’re brand-new to points or already flying regularly, you’ll get a practical, step-by-step gameplan to secure the companion pass and squeeze maximum value from it, plus intel on routes, hubs, and event meetups to level up your travel.
What you’ll learn
The cleanest timeline to lock the 2026 Southwest Companion Pass
Which credit cards to consider and how to sequence them
Points vs. flights: the math to qualify efficiently
Recent Southwest program changes (and what still works)
Hubs, routes, and positioning strategies
Opportunity cost: when not to chase it
Chapters
00:00 Intro
00:45 Meet Max Craig (Points to the Max)
02:50 Companion Pass, explained (eligibility & value)
04:49 Credit-card strategy & timing for 2026
06:10 What changed at Southwest (and what didn’t)
07:49 Qualifying: points vs. flight segments
11:22 App strategy: rules, pacing, and denials
23:35 Events, meetups, and community resources
28:47 Music City Miles & Points shoutouts
29:37 Frequent Traveler University notes
30:33 Fine print of the Companion Pass
32:55 Hubs, routes, positioning flights
34:53 Opportunity cost & alternative plays
43:10 Program benefits recap & pitfalls to avoid
43:36 Where to find Max (site & socials)
45:31 Trip planning tips & closing thoughts
51:31 Outro
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Rough Transcript:
Theme Song: [00:00:00] Travel at low cost with points and miles. Credit card rewards bring the smiles. Many adventures tells to be told, make and save money, the world will unfold.
Fight the war on happiness. Pick up the gold. Hurdy Gurdy Travel Podcast breaks the mold.
Justin Vacula: You’re listening to the Hurdy Gurdy Travel Podcast, I’m your host, Justin Vacula, here to help you make money, save money, and travel the world at next to no cost with credit card points, miles, benefits, and loyalty programs. Max Craig, Miles mentor Max, from points to the max.com joins me to talk about earning the Southwest companion pass in 2026.
Learn how to earn at least two years of effective [00:01:00] buy one get one flights for you and a guest. Visit meetup.com/philly miles and points to RSVP for monthly Greater Philadelphia Travel Credit miles and points meetups I host in Willow Grove, Pennsylvania. The next meetups are November 23rd and December 21st, 2025.
Find a link in the show notes for more content between shows. Follow Hurdy Gurdy Travel Podcast on Facebook and x. Follow Justin Vacula on Instagram. Subscribe to Hurdy Gurdy Travel podcast on YouTube for daily content, including travel videos, podcast clips, and posts. Find more information including select episode transcripts at hurdygurdytravel.com.
On with today’s episode recorded October 30th, 2025. Welcome to the show, max.
Max Craig: Thank you Justin. Nice to meet you in Chicago. We had a great time at Chicago Seminars.
Justin Vacula: Yeah. Excellent. And thanks for the ride back. It was nice to meet you in person to chat, spend [00:02:00] some time on the car ride and outside of it. So a really good time.
I think we had 375, 400 people,
Max Craig: organized chaos, I’ll call it. We’ve had definitely had four rooms going at once. Lots of people trying to switch rooms depending on what their interests were. It was pretty cool.
Justin Vacula: I like it. Great to meet some listeners of the show, some new faces including yours.
And all the attendees, lots of social events, educational sessions, and more. And we have an announcement for next year, Chicago Seminar’s, heritage Edition at Holiday Inn with a new name. It is the Chicago Points Travel Festival, October 16th through the 18th, 2026. You can use promo code Hurdy Gurdy for early bird discounts $40 off November 1st through the 30th.
So looking forward to that next year once again. But today we’re here mainly to chat about the Southwest Companion Pass, continuing this 2026 series as 2025 is [00:03:00] coming to an end. So for listeners, newer to Southwest, could you explain the Southwest Companion Pass in plain terms?
Max Craig: Sure. So it’s basically buy one, get one free flights for at least an entire year.
If you earn it really late in the year, you’re gonna get it for the remainder of the current year plus all of the following. So part of what we’re gonna talk about tonight. Is how to time it so you get the pass activated as early in the year as possible. Because if you get it very early in 2026, it will be good all the way and through the end of 2027, so almost for an entire two years, and your companion can travel.
For just the price of taxes. So for those domestic flights, they only have to pay the TSA fee of $5 and 60 cents for those international flights, the landing fees and all of that, that those international airports charge are unused. So it’s a little more when you go to Mexico and things like that, but the fair price [00:04:00] is absolutely free for your plus one.
Justin Vacula: And this is on cash rates, points rates, both. How is that working for listeners?
Max Craig: Absolutely. So it doesn’t matter if you pay cash or points, and that’s the huge benefit is even when you redeem your points, you can still add your plus one. There’s no additional cash outlay required is if it’s a 25,000 point flight, you both get to go for that 25,000.
And then just add that five 60 in fee. So that’s a huge benefit and especially when you get your 135,000 points to qualify is that you don’t need to save those points. You can actually redeem as you go. Your companion pass qualifying tracker only goes up. So you can redeem on the way when you’re trying to renew your pass in future years as well.
Justin Vacula: Great. So cash rates. You can use some cards like maybe the Venture X for a purchase eraser. You can use maybe points from Chase transfer to [00:05:00] Southwest or points earned from Southwest credit cards. Any other options that people can use.
Max Craig: Absolutely. So actually Built is now a partner of Southwest as well.
So as far as the card transfer partners, those are the ones, right? So it’s Chase and built. So those ultimate reward cards that, that earn from Chase as well as the built program. And then obviously the co-branded Southwest Direct Cards are all options for you to do that.
Justin Vacula: Great. So you have options instead of paying cold hard cash.
That’s nice that can be the case. And might there be any changes? In 2025 or changes coming in 2026 to the companion past that people should know about.
Max Craig: Actually, as far as qualifying, there’s been no changes announced, and when they did move it from 125,000, 135,000 points a few years back, they did tell us in late September.
So I think we’re safe for the 2026 and 2027 pass, although obviously anything can change going forward. But some people like myself, we’ve already [00:06:00] requalified for. For 2026. And a lot of people have been doing that basically since the beginning of 2025. So as far as right now, there’s no changes to the companion pass.
The big changes of the Southwest program start in late January of this year, and that’s when they go to assigned seating. So it won’t be the free for all and the boarding positions and all that stuff that it is today where you line up an order, they’re actually going to, I think it’s an eight boarding group kind of structure.
Where, but you’re still gotta go to your assigned seats
Justin Vacula: and there appear to be two different currencies or trackers or instruments, whatever we might wanna call them. I’m seeing here on one of the cards, there’s a companion pass, qualifying points boost, and then you’re also earning points with Flight with Southwest that you can book for flight.
Max Craig: Absolutely. So the companion Pass boost as part of that change I just mentioned is that when they went from 125,000 qualifying points to 135,000 is that they basically [00:07:00] gave all current cardholders that 10,000 point boost, and that comes. To everybody in January, as long as you have the card on 1231, everybody gets that 10,000 boost.
It’s companion pass. Qualifying only points, though there aren’t points that you can spend towards flights, but it does effectively lower that point threshold of you gotta earn 125,000 if you’re a card holder. So it lessens the hurdle a little bit.
Justin Vacula: Okay, so there’s qualification towards the companion pass.
Which would be spending on the card and then the cards give you a companion pass points boost. They use the word points twice. So maybe America loves confusion there a little bit, but we know America indeed loves math if it’s easier to get to that threshold.
Max Craig: Absolutely. Yep.
Justin Vacula: And can you talk more about the qualification process?
How you get the companion pass to begin with?
Max Craig: Absolutely. So it’s really, there’s really two metrics. We’re gonna talk mostly about the [00:08:00] 135,000 points. The other metric is a hundred flights, and it’s a hundred cash flights, right? So it’s so you don’t earn, you don’t earn basically the tier points or the companion points when you are flying on points to get a hundred revenue flights.
Chances are. You would get the 135,000 points anyways first. So we’re gonna talk about how to get the 135,000 ’cause that’s pretty much how anybody does it, is that there’s a lot of different ways to do it. The most traditional way is to do what I call the two card method, where you apply for basically one personal card and one business card.
Pretty much this time of year. And you time your spending. So you achieve those bonuses both as early in 2026 as possible, and between the two bonuses, that would add up to 130 5K. So that’s a great option for those that are new to the Southwest program and don’t [00:09:00] have cards currently because if you have, say, a personal card open, there’s some card rules there.
About a 24 month spacing between card bonuses and all of that. Is that for somebody fresh to the program, that is the traditional, what I’ll call straightforward path to basically time things appropriately. But for those renewing and those that are have had a card for a while, is that you can augment by doing a card bonus.
But you can also do card referrals. You can also do the shopping portal, you can do the dining program. Hotels is a huge one. So there’s a lot of people that don’t fly as much, but do use the Southwest Hotels platform and sometimes those can be up to 25 x on your spend. Is that’s a good way to rack up points to get to that 130 5K.
Justin Vacula: Okay, so it sounds like the answer to everything as usual is more credit cards. So you would probably do that two card method rather than taking all these flights unless [00:10:00] maybe you’re in a very special business situation where you’re getting reimbursed for travel. But even then probably you’d want to have those cards anyway I would think.
Max Craig: Correct. And that’s, and that was me and really still is me for many years. Is it traveling for work when you’re getting those qualifying flights? Is that I don’t generally need to do what I would say new credit cards to do it, because you’re always qualifying for that following year. So if you do enough flight volume in some, I would say at least mid-level spend on your card is that you always renew out a year.
But I realize that’s not for everyone. So those that get the pass, say for the up to two years, the initial time, they have lots of options on how to keep it right. So one option is to switch between your player one and player two. So your spouse, your travel buddy, whatever that is, would be your player.
Two is that they could do the two card method and then you’d have it for another two years. Or you could do, obviously you can do up to three cards, is that you can [00:11:00] switch. And get a different card bonus to pitch it out another year or reset the clock and go for two after your 24 month timeout. So there’s lots of options to not only get it but also to maintain it.
Within your household,
Justin Vacula: any particular order or priority. Of getting the business before the personal, before the business. What might that look like?
Max Craig: Usually, it really depends on your 5 24. And for those of you that aren’t familiar, the bank that issues these cards does count how many personal cards you’ve gotten in the last two years.
It’s really what I would call a velocity control thing that they have generally, for those that are, say three or four of 5 24 should. Definitely do the business card first. Business card does not increment on that count. And it can be a little more challenging to get, so you definitely wanna go to the business card first because if you are 4 24 and you get the personal card first, that puts you at five and they won’t give you the [00:12:00] business card.
So those that are 4 24, like pretty much have to do the business card first. But like right now, recently we’ve had some elevated personal card bonuses. So the traditional really, I would say, becomes more of a flow chart of which you do first. Should you take that elevated personal bonus and do that first?
It really depends on what your card velocity is with this bank and with others of which order you should go. But traditionally you do wanna do the business card first, then that way you know where you’re at.
Justin Vacula: Yes. And we’re in it for the long game. So we want to be strategic about the credit cards we get.
And with that 5 24 rule in mind. So for listeners, once again, that’s if you’ve been approved for five or more cards, appearing on your personal credit report is a quick and mostly accurate explanation of that, although there are some exceptions. If you’ve been approved for five or more cards in the last 24 months appearing on personal credit, then you can’t get cards with Chase.
So you want to be very careful about which cards you get early [00:13:00] on in this game. And if you really value that companion pass, then you would get maybe the business card, it wouldn’t add to the count, and then you get the personal card after just to be safe. Or if and you’re very confident you’re not at four, outta 24, then you can get that personal first and then the business.
Max Craig: Absolutely. Yeah. This is definitely a hobby that is a marathon, not a sprint. Sometimes people get a little too excited about elevated offers and aren’t thinking of what I would say step two and step three. And that’s another way I would say usually it matters more for those newer to the hobby.
Like they’re renewal is that they do get their companion pass and they keep going and grabbing other cards and when it comes time to renew the pass. They’re in a situation where it’s hard for them to get a card, or it’s not even possible because of their velocity in between. My recommendation is usually pick which person has to be, I would say, the pass holder in the future.
If that’s you, then you have to be more in [00:14:00] control than your P two. If you’re gonna be switching to your P two, then P two has to be really more deliberate about their card volume and their card velocity, if they’re gonna be the ones that you switch to once your pass does expire.
Justin Vacula: Yes, and that’s the player too.
So that’s usually an enthusiastic participant or maybe not as enthusiastic, but they go along with it anyway in points and miles. But hopefully after seeing all the results of travel and away from the theory of it all. There’ll be more enthusiastic.
Max Craig: Absolutely. Yeah. The player twos are usually enticed once they start flying for free or you take them to Europe or something.
In business class, is it a reluctant P two of I don’t wanna apply for too many cards. Somehow becomes of what do we need to do? So we can do that again type conversation. Yes. We could probably do a podcast just on how to position your P two. Is that how they, how to get them as a bigger participant.
How to motivate them to, to play this game with you instead of being the more passive participant.
Justin Vacula: Great. And what do you think are [00:15:00] some of the better credit cards that the listeners should consider? It seems like there are a lot of them, A lot of Southwest credit cards.
Max Craig: There are, there’s quite a few.
So there’s three personal cards and there’s two main business cards. And actually they’re coming out with a debit card. That’s really fairly recent news. But the, generally, I suggest, especially on the personal side, the highest personal card. Of course, it is also the highest fee. But what it does do, especially as we move into a.
Assigned seating world, it allows you to get those seat assignments at the time of booking. So those of you that don’t have status where you’re, where you get those at booking type benefits for either preferred or extended leg room seats, is that’s a perfect option to get those preferred seats and standard seats at time of booking.
So you don’t have to do what I would say the scramble at 48 hours. So currently the process right now is boarding order at 24. But going forward, it’s going to be the, at [00:16:00] 48 hours pre-flight is that people are gonna be able to switch and try to go in for seat assignments. So it’ll be what I would call that typical first come first serve type of activity is that, I think that’s a, I’ll call it a small price to pay.
For the uncertainty and the having to be fast on the computer and things like that at the time of booking. It also has some of the best multipliers to not only get more points, but also have more companion pass points accumulate. So that one is definitely the best as far as business cards. It can go either way.
So when I talked about the two card method a little bit ago, is that generally. When you’re doing the two card method I suggest doing that highest personal card and actually the lower kind of business card. And the reason for that is the signup bonus volume is that generally the business cards either go to elevated hand in hand with each other, or the higher business card actually gets a higher elevated bonus.
So when you’re trying to renew next time, [00:17:00] I usually like to promote saving that higher bonus. Business card for next time because there’s no bonus for getting 150 or 160 qualifying points in one time. Is it that way you save that card? That can be, usually those bonuses we see on the higher business card are in the 80 to 120,000 range.
So actually sometimes you can get your pass renewed. With just that one business card. So that gives you future flexibility. Like when we’re talking about playing the long game and playing that marathon game, is that’s part of the overall strategy is to save that card for later. So you have that option.
Justin Vacula: And we’re looking at perhaps applying for these cards in November or December. We’re recording at the end of October, 2025. So I’ve heard a lot of people say the welcome offer needs something like 4K spend, for example. And they’ll spend somewhere around three K to not hit that spend goal early. Because [00:18:00] as it’s my understanding, you want the spend to finally post to hit that welcome offer in early January.
So can you talk about that?
Max Craig: Absolutely. So generally the minimum spend offers are three months. Sometimes we see five and even six months, but generally it’s three. So really this time of year, like we’re recording this, the, basically the day before Halloween here, the end of 25. Is that, this is the time you can start doing that is that because of the 90 day spend threshold is that your 90 days will go into early 2026, so you can time your spending appropriately.
And that’s definitely what I generally suggest is you gotta make sure that you stay far enough away from the minimum spend achievement, because that’s the one thing that’s, I’ll call it hard to watch. Is that people do overspend or say somebody else is, has tapped to pay on their phone and they, oh gee.
And they use the card. Oh, yeah. P two messes it up. Oh no. [00:19:00] Don’t do it. It, unfortunately, it does happen. And it’s not always P two. It can happen that it’s P two, but it could be some recurring bill. Is it? Oh, I, my insurance only hits. Every six months. Oh, and it’s like for the auto pay on there’s, yep.
My car insurance renewed in December and now I got all my points in December. So I have a pass for 12 and a half months instead of 23 and a half. So those things do happen. I actually have, actually, now it’s two infographics about how to avoid those types of danger zones. The other big one. And there is a spend tracker in the bank’s app that shows you how you go.
People think that, Hey, my bill was 3000, so I’m fine, but if you bought something for $500 and returned it. That counts. Your spend tracker only goes upward. So even though you don’t owe that, it still counts. So there’s people that say Hey, I didn’t go over 4,000 because I pay my bill in full and I never paid more than four.[00:20:00]
But because of buying and returning type of activity is the spend tracker says 5,000, even though they only ever paid say three or 3,500 on the card. So that’s another. Danger zone that I try to make people aware of is to make sure you understand how those spend trackers work and make sure that you don’t have it.
The one that’s a little out of our control, and part of the reason why a lot of us kind of point junkies it stay away by a thousand dollars is because a double payment can send you over too. So say a vendor accidentally swipes your card and both payments post. Is that counts even if it’s reversed.
So you definitely wanna sock drawer the card once you get close and make sure that once we get into 2026 that you continue. So make sure you don’t have those auto pays sitting there that are gonna accidentally put you over. Just put the card away once you [00:21:00] have enough, and know that, say that last thousand Hey, I’ll just prepay my utilities and I’ll be there.
Is that, make sure you do that right away. So the other big thing that I wanna mention here is. Card closing dates is that card closing date is the key is that the bank only posts points to Southwest once per month. So you definitely need to know what your statement due dates are and what your statement close date is if you hit those, spend thresholds before your statement close date.
And you’re gonna get the points on that date to know what that is definitely key. Get to change that date. If you don’t like what you have, you get to change it once per 180 days. So if you get a card, say you get the card, now is, it is, you can’t change your first one because that one’s automatic, but you get a chance to change it.
So say you wanna. Target mid-January is a, is you could theoretically change your statement close to be that if necessary. So you definitely wanna understand how [00:22:00] that works. So not only you get your spend in on time before your 90 days is up, but you also have basically certainty of when your points are gonna post and you’ll hit your achievement.
Justin Vacula: We don’t want any Halloween horror stories or if you’re listening closer to Christmas Cole in the stalking because you messed this up or someone else messed it up on you. Just be precise. Be careful to do this in the proper way, and we certainly don’t want a lifetime achievement award of losing some things because of too much spending or too much applications, as I believe the usual idea is to spread out the applications of these cards.
Maybe wait 30 days in between cards or even as much as 60 or 90. Between because maybe if you go for five chase cards in the same day, they’re not gonna that and probably shut you down.
Max Craig: Absolutely. So they, chase actually has a, what’s called a two 30 rule. The max they will give you is two cards in 30 days.
So if you do one, say, now we’re [00:23:00] talking around Halloween time is to do one another, one say closer to Christmas. Because you can still a achieve your spend all on that first statement and that’s totally fine. ’cause your first statement will cut in January. So you’re you definitely have time and you don’t wanna do them too fast and too close together because that second one might go under review is Hey, why do you need two cards that are close together?
A lot of times it’s better not to have the bank put eyes on some of the stuff that we’re doing is that let’s try to keep our odds high for automatic computer approval.
Justin Vacula: All right. Very good. We will take a quick break with messages from our sponsors and announcements. Join me at Zork Fest 2025 in Las Vegas, December 5th through the seventh at M Resort Casino Hotel. Zork Fest combines miles points and gambling content all in one weekend.
I’ll be there speaking and connecting with podcast listeners. Buy your ticket at Zorkfest.travelzork.com. Use [00:24:00] the promo code HurdyGurdy to support the show. And Max, will you be in Las Vegas in December?
Max Craig: I unfortunately will not. I won’t be able to make it that weekend. But I do hope to attend next year.
Justin Vacula: All right. And I have various Chase Sapphire Reserve benefits ready to go in Vegas. I wrote an article about that for travel zork.com. So maybe you too will be using benefits, going to sphere, having these fancy dinners. Anything else, any plans for Vegas in the future?
Max Craig: I don’t at the moment. Usually I end up in Vegas for conferences.
I’m not as big of a gambler as you are, but I do love Vegas. I do love the shows. I do love the vibe.
Justin Vacula: All right, maybe we’ll get you to sign up for an MGM credit card in January. We’ll see
Max Craig: Potentially. I’m always open to that.
Justin Vacula: All right. And Chicago Seminars event at Hyatt Regency O’Hare Approaches: November 7th through the ninth, 2025.
[00:25:00] Use the promo code HurdyGurdy when buying a ticket to support me. And will you be at Chicago Seminars Hyatt Regency O’Hare.
Max Craig: I absolutely will. I look forward to it. That’s coming up here in just over a week. But yeah, that should be a great time. And another huge meeting of a bunch of other point aficionados.
It’ll be great.
Justin Vacula: The social gatherings, the parties and so on went on. So that’s a nice thing about the community. A lot of. Social events and not just informational sessions. Everybody goes back to the room and that’s it.
Max Craig: I was very good in the other Chicago seminar on Saturday night because my speaking engagement was Sunday morning.
I was right after the kickoff. So I had to be very diligent on that Saturday night.
Justin Vacula: Great. And this episode is also supported by CardPointers. If you have multiple credit cards like me, because of course the answer to everything is more credit cards. CardPointers helps you automatically activate bank offers and knows which card to use for maximum rewards card pointers, saves me time and money.
Use my link CardPointers.com/HurdyGurdyTravel [00:26:00] for a discount on annual and lifetime plans. And you’ve been a user of card pointers for a while?
Max Craig: Oh, quite a while. Probably close to a decade now. Especially as you get more and more cards to keep track of everything. Is that it’s a wonderful tool.
And is, and I use it all the time. I think I have. Probably over 700 current offers loaded into the card. So definitely use the features that are in that app to make your own groups and favorite your go-to stores. Because as you get more and more cards is that it can be overwhelming and that really.
I would say lessened my need on having some crazy spreadsheets of keeping track of what’s on promo. What’s the best multiplier? Oh, this multiplier is elevated for three months, is that they do that kind of stuff for us and it’s a huge benefit to managing what I would call my chaos.
Justin Vacula: I like it. You might not be going to sunglass hut with an Amex offer or a speedway hut, but a lot of these bank linked offers can be quite good, especially I’ve seen a lot [00:27:00] of nice ones for.
Lowe’s post office, UPS store and so many more it’s nice and you get the occasional accidental surprise where you spend something you don’t realize it was an offer and then oh, you’ve received cashback or points.
Max Craig: Absolutely. Those are always great surprises. Especially a lot of times it like if I’m spending more than say a hundred dollars, I usually take a look, but sometimes it’s just ah, whatever.
And you swipe it and then yeah, you get that email notification and you didn’t know that you added the offer. ’cause card pointers did it for you and that’s fantastic ’cause you would’ve missed it. You ’cause you a lot of those offers if you don’t activate them. You don’t get it right. So card pointers activates it for you and you get that nice surprise that you earned a few points that you otherwise would’ve missed.
Justin Vacula: And we met Brooke from card Pointers in Chicago as well with the card pointers. Purple. Similar to past podcast guest Purple Princess Pari Kim from the show, love on the Spectrum. Happy to give her a shout out as she’s supporting of the show. So card pointers for the win and [00:28:00] toss Pari a follow on Instagram, purple Princess
Pari and next we have monthly travel and points meetups in Willow Grove, Pennsylvania. Next meetups are November 23rd and December 21st, 2025. If you’re local or wanna make the trip, it’s a fun casual way to talk point strategies. Meet like-minded travelers and share ideas. RSVP at meetup.com/philly
miles and points, and in addition to meetings, I’ve added new social events, including a meetup in Las Vegas before Zork Fest. So Max, will you be in the Philadelphia area or do you have local meetup groups?
Max Craig: I will not be in the Philadelphia area anytime soon. I’m usually there a couple times a year. And I don’t know, but maybe we can make that an overlap where I can stop in when I’m there for my day job.
But yeah, so we do have music City Miles and Points. I actually live in the Nashville area, so there is a Music City, miles and Points Facebook group. So for those of you. That are in that group or should be in that group? [00:29:00] Definitely give us a find on Facebook. And then there’s also there’s some groups in both Chattanooga and Knoxville as well.
And as a result of the Chicago seminars, we just got done with. We’re talking about potentially having not a full weekend event like we do in Chicago, but maybe a Saturday event where people do come in from the cities that are a few hours out. And we all do a bigger meetup than just our little evening, have a couple of beers and chat type of things that we usually do.
Justin Vacula: Nice. And once again, if you could say that Facebook group.
Max Craig: Yes. It’s called Music City Miles and Points. And it’s on Facebook. You should be able to find it pretty easily.
Justin Vacula: Excellent. Finally, I’ll be speaking at Frequent Traveler University, FTU Dallas, Irving, Texas, just outside of Dallas from May 1st through the third 2026 at the Nylo Las Colinas Hotel by Hilton.
Join me and community members for social events and educational sessions. Ticket sales are live: $200 for FTU [00:30:00] members and $249 for non-members. You can grab an FTU annual membership for online courses, seminars, member perks, event discounts, and more. Sign up link for membership, and FTU Dallas is in the show notes.
And do you plan on going to FTU Dallas or have you been at one before?
Max Craig: I have not been at one before, but I definitely do plan on looking more into it. Definitely intriguing and I think that time of year can work for me. Once it gets into June and July, it’s hard. But early, early May should be definitely be doable.
Justin Vacula: Ah, excellent. Okay, we’ll return to the show here with Max Craig Miles, mentor Max from points to the max.com. We’re talking about the Southwest Companion Pass, particularly in 2026. So we get the companion pass. You have a companion in mind. Can you change companions? How many companions can you change?
Max Craig: You can change your companion.
So you actually get one [00:31:00] designation. Once you earn your companion pass, you get to designate your companion. So that actually doesn’t count as your change, that’s your quote unquote initialization. And then you can change it three times in per calendar year. No matter if you have a temporary pass or you have a full pass, is that you get three changes per year.
But it is not that you get to have. Three people and you get to change in between trips. You can only have one companion booked at a time. So if you go from companion A to B and back to a that, that counts both directions. So it counts one switch away from a and it counts one switch back to a. So that’s something to keep in mind with your overall strategy of how you do that.
So traditionally my player two, my wife is my companion but she is not a Alpine skier. So usually once a year I take a buddy out to Colorado or somewhere else to go skiing. So I will switch it for that trip away from her, take my [00:32:00] buddy, and then switch it back to her once I come back. So a lot of times I don’t use that third change, but I do the change away from her and then the change back to her to basically fly.
A a friend out to go skiing. So that’s part of how it works. So you definitely wanna strategize over the year of how you do wanna use those changes. So say you have a few different people that you wanna include, you wanna make sure that if you can’t basically change to everybody, that you pick the trips that are likely, the ones that are more expensive, either on points or on cash.
So you get the most value because those other trips that you don’t have enough changes. To bring somebody different. You generally want those to be those cheaper trips.
Justin Vacula: Good to have options. You never know what might happen. Maybe the reluctant player too won’t want to travel at all, and you just say, okay, if you don’t want to travel, I’ll just go with someone else.
So you’re not tied to that companion. So that’s a nice thing.
Max Craig: Absolutely.
Justin Vacula: And which airports do you think might be best for this? How about East Coast people? [00:33:00] Especially those flying out of Philly? Where we have the wonderful new or now new-ish Chase Sapphire Lounge.
Max Craig: Philly is a decent option for Southwest and especially if you can get in the Sapphire Lounge on either a Sapphire card or the Ritz Carlton card.
That’s a good option and I love that lounge and the food is good. The drinks are awesome. Is that, it really is, I would say a. Airport dependent thing. So you definitely want, usually a decent Southwest presence, but even for those that are in airports that aren’t, say, dominated by Southwest in the bigger hub cities.
I know Southwest likes to not use the hub word. But reality is that airports like Baltimore some synonym. How about
Justin Vacula: synonyms?
Max Craig: Yeah, so they call it a wheel and spoke or whatever. I don’t know what they make up names, right? So a hive. Yeah so BWI is definitely would be one of the East coast hubs and then obviously midway in, in Nashville and then Vegas.
Denver is that they [00:34:00] definitely have a lot of hubs outside of the traditional, everybody thinks the Southwest is being Texas based. But they do have. Quite a few hubs throughout the country that they work with. So it doesn’t mean that you have to be at one. It means that you have to be able to usually get to one pretty easy.
So like for those of us that are in the Tennessee area, is that they are starting on Knoxville. Flight, I think it starts in early March. So that’ll give Knoxville people not only an option to get to Nashville, but to, to Baltimore and I think Denver as well, to basically get those smaller market cities plugged into their overall network.
So similar to what the other airlines do with regional jets and some of the subcontractor type airlines that they have, is that they really are trying to feed in from some of the smaller footprint airports into those hubs.
Justin Vacula: All right, so let’s play devil’s advocate for a bit, not quite the Dave Ramsey devil’s advocate, but what might be the opportunity cost of focusing [00:35:00] on Southwest?
Might we be losing out on other Chase cards or spending towards other goals?
Max Craig: You definitely
Justin Vacula: always have to,
Max Craig: I would say think of the big picture, right? There is an opportunity cost, especially if you’re doing the two card method is that you’re gonna use one of your personal card slots for sure and a business card.
Slot. And for those of you that don’t know, in the last year or so, chase has started to pump the brakes a bit on business card approvals, especially for those of you that apply as sole proprietors. It looks like that general gauge is around three business cards say in that, say. Yes. War on happiness.
It’s definitely a war on happiness. The days of getting chasing cards every other month and doing that for a couple years are definitely in the past. So that war on happiness is something that is current news, right? There is an opportunity cost, and that’s part of the reason. Why I’m a fan after you do, if you’re brand new, the two card method, there’s really no, no harm in that [00:36:00] long term.
But if you’ve been in the game a while and you have a fair amount of cards, the two card method might be harder for you to use as a renewal tactic. Is you’d have to get two cards relatively close together again. So I’m a big fan of trying to do it with one card plus some other activities, whether that’s flying the hotel stays, leveraging the shopping portal, dining program.
There’s all kinds of ways to feed in to get to that 1 35 because. It’s not as, I would say, flexible as it used to be to just go grab two cards every other year and keep it going. So there is definitely some long-term challenges with card velocity. And to go back to your initial question.
Is that there’s always opportunity costs, right? As I could have done if I was doing two cards, I could have done a different card and done a completely different program. Is that, those are always options, right? But I still do think even with some of the, what I would say, unpleasant changes like Southwest starting to charge for bags and things like that.[00:37:00]
That’s something I didn’t mention earlier. But all of these cards come with. Not only one bag for you, the card holder, but also for everybody that’s on your reservation, including your companion up to eight. So if you’re traveling as a group of nine people, which probably don’t do, America loves math. Yep.
Everybody gets. A bag allowance. So that one annual fee will probably be paid for in one trip. So even if you only travel and say 2, 3, 4 people, is that annual fee is gonna be less than those bag fees would very fast. So that’s something to consider, bring, consider and
Justin Vacula: carry on, bring 10 pairs of shoes, yep. Let’s see what we could do. Can we put some luggage on the roof of the Uber? Is that an option? Yes.
Max Craig: So definitely. Some of y’all probably need to get the Uber XL if you’re bringing lots of luggage, but yeah, the days of everything being two bags as obvi obviously ended this past, I think it was May.
That’s a change. It really doesn’t affect me as much because [00:38:00] I do still get two bags because of status. But for those of you that did do ski trips and things like that to try to get all your ski gear in one bag. Eh, it’s a little more challenging. Ah, but it is still, but still holding a card. And I think that’s part of the reason why they attached it to the card is to reduce some of the churning that some of us do, is that you keep at least one of those cards open.
‘Cause they know that a lot of us do the burst mode and get two cards is to keep one open, perpetually to keep those assigned seating and those baggage benefits.
Justin Vacula: Why did you rent the Stretch Hummer in Las Vegas? We just needed all the musical instruments we brought with us so we can finally play the Hurdy Gerdy in front of the Bellagio Fountain.
Awesome. Yeah, the check bags are pretty nice. I think that especially if you’re traveling with multiple people, that’s a cold benefit that they give that much. Some others might be more restrictive as just one bag of person or a total on the reservation of a smaller number.
Max Craig: Absolutely. Yeah. So there’s a fair amount of cards out there that, that do give [00:39:00] a bag benefit.
With their membership cards as well. And to me, Southwest just aligned to that kind of model. I still think that it’s pretty flexible as far as how they treated some of these changes.
Justin Vacula: So the answer besides more credit cards is usually, it depends, what are your goals? What do you want to do?
Are you going be spending heavy at office supply stores than maybe the ink cash card? Could be a higher priority maybe if you’re staying at Hyatt Hotels a lot and you value the Hyatt status that might be up there, the sapphire cards might be up there, so it’s getting tougher with the approvals. So for people who’ve been in the game.
We’ve had it easy, but now it’s gonna get a little bit stricter in the future probably.
Max Craig: Absolutely. And that’s one thing that I actually have even done webinars on it myself is that combining basically a Southwest companion pass with those cards that are an ultimate reward. So you can use those points to go to Europe, you can use those points to go to Hyatt.
They all work hand in hand. So it’s really, I [00:40:00] would say, the priority of what’s first. Because the answer is probably all of the above, but it really comes down to which order. Like getting by one, get one flights to say ski locations and domestic locations and going to take a beach vacation in Mexico or whatever your beach of choice is on Southwest.
Gives you lots of options, but currently Southwest. Fly over the Atlantic or the Pacific, right? You can get part of the way there to Hawaii but you can’t get all the way to Asia, right? Is that a lot of people do wanna go and take those, what I would call bucket list trips. And that’s where you might actually do a repositioning trip to say LA and even take a repositioning trip to Hawaii.
Basically leave from Hawaii to Asia, leveraging your companion pass. So they do work hand in hand and they work hand in hand quite well. But yeah, that’s part of the, which order do you go conundrum? I would put it, yes. No, it’s not really a binary decision. It’s really which order do you go and I think by one, get one flight.[00:41:00]
I value that more than Hyatt status. As much as I love Hyatt is that I lock in basically my companion pass and have basically a plan for that, and then I switch to switch gears to chasing those transferrable points, chasing those hotel statuses, et cetera.
Justin Vacula: Pun completely intended.
Max Craig: Absolutely,
Justin Vacula: and I like your beach of choice.
That’s a good one. Perhaps I’ll be in Atlantis January, 2020 sixth, the 14th through the 18th. I’m almost at seven Stars status with Caesars. I haven’t booked anything yet, but I’m looking at booking those to get more benefits when I do the booking, rather than booking now with Diamond Elite status. So maybe even Southwest can get you to The Bahamas, or at least get you to Florida first.
Max Craig: Absolutely. Yep.
Justin Vacula: Both on that Bahamas and Florida.
Max Craig: I’m not, I haven’t been to The Bahamas on Southwest in a bit. But I definitely can get to many places in [00:42:00] Florida. You definitely can get to Jamaica, Cancun, and some of the others that I’ve visited recently. Great. I think Martin might be a relatively new one that’s coming to Southwest.
I’ll have to take a look at that.
Justin Vacula: And how about Belize? We mentioned him. It’s mandatory. Dave Ramsey said he can’t get to Belize on miles and points and all these blackout dates. Don’t you know? And all your points are gonna expire and you have to spend $300,000 to get anything.
Max Craig: Oh yeah, he, his credit card hate is real.
If he knew how much travel we were doing for how little spend, I, maybe he would change his tune. But I think he’s not changing. It’s like bad strategy.
Justin Vacula: Yeah. Bad strategy from Dave. It’s like a poker player that goes up to the table and says, oh, this game sucks because I went all in every hand and I lost my money.
Max Craig: That’s the weird part is if you don’t know how to play the game, you just plan about the game. But yeah, we don’t, I don’t spend anywhere near that and can take some ridiculous trips.
Justin Vacula: Dave Ramsey debunked in one minute. [00:43:00] Pretty much. Great. So anything else that you’d like to add before we close out and we’ll give you an opportunity to promote yours as well.
Anything else you’d like to add to the Southwest discussion?
Max Craig: No, I think that the program changes have been, I would say, gave a little bit of a negative cloud because I think Southwest was basically, I would say, a differentiator. But I think that biggest differentiator is the companion pass, and it looks like it’s here to stay, at least for now.
So I think that’s huge. And they’re definitely rewarding card members for doing that, is that the cards actually come with, I would say, quite solid value. So definitely look at my page, which is called Optimize Southwest. It’s called Companion Pass and Rapid Rewards. So that’s a full name.
My creator account is Max Craig, MAX. C-R-A-I-G. So that is a public creator account on Facebook. The optimized Southwest page is on Facebook as well. Is that’s where I have a lot of my Southwest based content. But I also do have a [00:44:00] transferable points page as well where we talk about how to get those flexible points so you can redeem at places like Hyatt get those international airlines you might have never flown on before, but you can fly them on points and that’s called.
Not a shocker, optimize transferable points. Is that’s on Facebook as well? I’ll be expanding in the next few months to put some more effort in the Instagram, but at this point I’m mainly Facebook focused.
Justin Vacula: And points to
Max Craig: the max.com. That is my website. There’s a few blog posts on there.
But most of my, what I would say, my favorite cards for different use cases, like elevated offers versus favorite cards for getting TSA for free and all of that, those are on the website, so that’s where. That’s where you’ll find I would say the deals that are going on when it comes to cards.
There’s also some blog content on there as well. But most of my fresh, I’ll call it more educational content. I do basically run it through the social pages first. [00:45:00] But again, that’s another project of mine is to cross post those as blogs on the page. I’m just not quite there yet.
Justin Vacula: All right, great.
And we invite listeners, as usual, chime in the comments, any questions for us? Thoughts on the value of Southwest and the Companion Pass in 2026. So thanks for joining me today, max Craig of points to the max.com. We’ll see you shortly in Chicago again.
Max Craig: Absolutely. But no, I’m gonna be probably driving back and forth but definitely would love to meet up.
Are you coming in on Thursday?
Justin Vacula: I’m arriving the night before. I’ve, I made a personal rule to arrive at events the night before, so I’m not rushing in the morning getting issues of delayed flights and so on. Are you staying at the Hyatt? I will be at the host property. Yep.
Max Craig: That’s a great area and a great location.
Because it there’s a bunch of stuff around there, like restaurants are close and things like that. So I think the the post [00:46:00] game will be lit. I got a feeling of people are gonna be enjoying that. I actually wish it wasn’t after Halloween, because on Thursday nights in the summer is that they, do they have national, like bands that come and play. So at, it’s called Parkway Park Bank. It’s like literally right around the corner from there. Is that it? That would be, it would be great, but of course probably couldn’t get it. ’cause that’s like conference time season. And that’s why they have those bands is that people are there for conferences and because there’s a band, it fills up all the restaurants and the bars make a bunch of money setting up bars outside.
But yeah we go down there. Quite a bit in the summer because we spend most of our time in Wisconsin June, July, August. ’cause Nashville is a little on the warm side and we still have that, my old bachelor condo from 25 years ago.
Justin Vacula: I remember on some cruises, I’d be walking past restaurants and there would be roving mariachi bands and they would just go up to people and play and try to get some tips.
So maybe that would happen too. You’re just eating [00:47:00] at a restaurant and all of a sudden a mariachi band.
Max Craig: We, I was actually in Belgrade, Serbia, probably a month back actually. It was about exactly a month and there was a traveling band that would, they were doing basically on request type of music, like four four piece band playing for, oh, playing for a Fiverr per song.
So it’s a good way for the make, make the night more interesting. And I think it was, I think it was like a Thursday night or something. It was relatively, I would say, medium filled restaurant, but it definitely was a nice addition to the visit in a country that I’d never been to before.
Justin Vacula: If you can’t see Taylor Swift in person, you might get the roving band with their cover songs.
Max Craig: My wife’s friends came down to Nashville from Milwaukee for Taylor Swift and asked if we wanted to go, and I told my wife no, especially not at that price. Absolutely not. So we went out to like lunch with them and then I, whatever. I took ’em and dropped ’em off at the stadium. I’m just like, I’m like, don’t park at the stadium ’cause you’re like a 20 minute walk to get to your [00:48:00] hotel from the stadium.
I’m like, we’ll drop you off. Leave your car at your Airbnb, we’ll drop you off. And then just. Work your way back to your hotel. Walk 10 minutes, stop at a bar, have a drink. Oh yeah.
Justin Vacula: Traffic chaos. You, I’m like, you’ll, oh, driving you. Especially
Max Craig: for Taylor Swift. It probably took 90 minutes just for the first 10,000 cars to get out of there.
Some of those people were probably locked in traffic for up to two hours. Because people come especially for Taylor Swift, right? Some people are there three or four in the afternoon. Oh yeah. 7:00 PM show is that everybody comes over a couple hour period, but then everybody leaves obviously when it’s done.
So it’s just chaos in, in, I don’t know how familiar you’re with Nashville, but there’s really two ways over the river, over the Cumberland River and the one is right next to Titan Stadium. So they actually close down the bridge to two-way traffic, everybody out. So that means that an Uber trying to get you back in has to go over the other bridge and basically, do we.
So it, that’s sounds terrible. It’s terrible. And Airbnbs, or not Airbnbs [00:49:00] that Ubers and Rideshare go instantly into surge, especially for something that huge. So it’s just yeah, you should just walk into town and grab a drink and get the Uber and an hour after the show or an hour and a half after the show.
Just go chill out if you’re not staying downtown.
Justin Vacula: I got out of Allegiant Stadium in Vegas, if I’m saying that correctly. And I saw people trying to get rideshare right after the event. I think I want no part of that. I walked to Luxor, I ate at the restaurant, hung out there, and then. Got the ride share and it was like two hours later.
It was just much, much better.
Max Craig: We were caught up in that Southwest debacle where their computers went down between Christmas and New Year’s. That one year, it was like two years ago, is we were supposed to fly back to Nashville, like on the 27th, and they were down and we, the first flight back that had availability was basically New Year’s Eve.
So we’d land at 10 30. On New Year’s Eve and 35 miles out is that we usually just, basically just Uber because [00:50:00] it’s more convenient because especially parking for a week is gonna cost as much as the two Ubers and obviously the Uber’s, whatever, more convenient, drops you off right at the right, at the check-in counter right is that we landed at 10 30 and I’m just like, oh, we’ll just, and it was a Saturday night.
Oh just Uber Home. It was a, it was 170 on Lyft and like two 20 on Uber. Oh. And I’m just like, and I’m just like, oh no. I’m just like, I’m not doing that. And it’s because now Nashville basically has. The central time zone dropped the ball stuff on TV now. So now a ton of people come here to do New Year’s E Fest.
And the people were at least smart enough to not drive, but that meant that everybody was moving around in Rideshare. And I’m just like, I’m just like, honey, I can’t do it. I’m just like, we’re going to Hertz. So we just wented a
Justin Vacula: car.
Max Craig: We just rented a car. But the problem with renting the car, we ended up with it for two days.
Because our little Hertz local edition isn’t open [00:51:00] on a Sunday, especially when that Sunday is New Year’s Day, so I couldn’t return it till Monday. But still at our corp at my corporate rate the two days of the rental car was, I think it’s 90, I think it’s like 45. 50 bucks with tax is that, that was way cheaper than the ride share, but way less convenient.
’cause obviously it was convenient just to drive the rental car home. But then we have to go drop it off. It’s 15, 20 minutes away and both of us have to go. She has to basically follow me. Is that, it’s just more hassle, which is why we try not to do it that way.
Justin Vacula: More trade offs. And I must say for musical suggestions, I have an older episode where.
I met a Herty Gerdy player, Anna Murphy of the Band Cellar Darling, and have an interview with her as an earlier episode, and I’ve really been into the band Reina, R-E-M-I-N-A. They have a YouTube channel at Ghost Bird Studios, and they recently came out with a new album called The Silver Sea, and a musical video, silence in the Silver Sea.
Love
Max Craig: it.
Justin Vacula: All right. [00:52:00] Thank you for joining me today. Awesome. Appreciate it Justin, and thanks everyone for listening. Stay tuned for future episodes. For more content between shows, follow Hurdy Gurdy Travel Podcast on Facebook and x. Follow Justin Vacula on Instagram. Subscribe to Hurdy Gurdy Travel podcast on YouTube for daily content, including travel videos, podcast clips and posts.
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