Alex: We’ve had some pretty incredible travel days thanks to points, but we’ve also had some pretty stressful travel days. Today, we’re sharing our best and worst travel days on points, plus what to do when things go wrong.

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Alex: We’ve had some pretty incredible travel days thanks to points, but we’ve also had some pretty stressful travel days. Today we’re sharing our best and worst travel days on points, plus what to do when things go wrong.

Alex: Hey, I’m Alex.

Pam: And I’m Pam, Alex’s mom.

Jess: And I’m Jess. Let’s talk points. Today, we are each sharing our best and worst travel days on points. Thankfully, we’ve had way more good travel days than bad travel days, but the bad ones are hard to forget. And you’re going to hear about mine and Alex’s worst travel day, and both of mine, like the one Alex is going to talk about, which is technically also mine, and mine.

Alex: Oh, I’m not talking about that one.

Jess: Okay, then I’ll talk about that one. But yeah, both of mine happened like within the last year, and so it’s, they are hard to forget. And we are going to share some tips for what to do when your travel day takes a turn for the worse. So we’re going to start off on a good note. We’re going to start off with our best travel days. So Pam, why don’t you kick it off and tell us about your best travel day ever?

Pam: Okay. So, you know, first of all, let’s start with what makes a good travel day for me. That is going to be an aspirational flight, flying something that I’ve just dreamed about for forever. Obviously, it’s going to be business class or even better, first class. It’s going to involve going to a great airport lounge. It’s going to involve everything happening on time and no delays.

And so my best travel date day to date, it was when I flew Singapore Suites JFK to Frankfurt. I had seen these huge suites before on Singapore, and basically you’re like in a room. You’re like in a small or a big bathroom size. You know, you’re in your own room.

You’ve got a leather chair that you sit in, and it swivels, and this humongous TV, like a TV I would have in my bedroom, and you watch TV from there. You’ve then got plenty of storage. You’ve got a bed that’s not your chair. It’s completely separate. It’s against the wall, and it folds down. And you have got the best staff. I mean, the crew, amazing. They cannot do anything more for you. They fall all over themselves in trying to help you. I swear. Of course, I think this is about Singapore Suites flight attendants on business class, and even in the other classes, they are attentive. I mean, if you clear your throat, they’re practically right there saying, can I get you anything? They are, they are amazing.

So I found this deal is 143.5k points for this flight. It was Singapore, I mean, it was JFK to Frankfurt. So obviously I had to position to JFK. And I was going to head over to London anyway, and I said, Alex, do you want to go? Maybe we can go to Paris or somewhere, and we can do a few days in Paris before I go over to London. She was able to find business class seats, and so that’s what we decided to do.

All of the flexible currencies transfer to Singapore Suites, making it really easy to get those points, those miles. And in fact, just one big Amex Business Platinum welcome offer covered that, my best flight ever. And I’ve flown some pretty amazing ones.

Alex: You know, and it can be hard to be like, oh, that’s a lot of money to spend on a flight. But when you’re on the Amex gravy train for the business Platinums, it’s a little easier to splurge because you’re like, yeah, I’ve gotten three of these. I can use one of them for a bucket list experience.

Pam: Yeah. Yeah, everybody should at some point. So I can remember getting in there, sitting down on my chair, and they offered me caviar. And I’m like, well, why not? I’m in Singapore Suites. Let’s try it. And surprisingly, it didn’t have a lot of taste to me. So it was all the things that went with it, the cheese, the crackers.

Jess: You got to have the sides.

Pam: Yeah, it was great. You know, unfortunately, I shouldn’t say unfortunately, but I don’t drink, because I’m sure that the champagne or whatever they offer there would have been over the top amazing. I just got some sort of a mocktail, but you know, I was just sitting there in my big leather chair and thinking, this is the life. And I didn’t even want to go to sleep because… but I knew that I had to at some point go to sleep because we were going to travel on from JFK to, I mean, not from JFK to, from Frankfurt to Paris, and hit the ground running, and I had to be ready to do it.

I was able to go to two lounges there. I went to the Virgin Atlantic and then the Amex Centurion just because I had the card to get to do that. Now there’s a Capital One lounge there, so I could have done that too. I really could have done some hotel lounging, because hopping, because I actually got there pretty darn early. I did not want to miss this flight for anything.

So I really, like I said, I stayed up as late as I could until I had about four hours left, and then my cute little flight attendant made up my bed for me. I got my jammies on. I went to one of the two huge bathrooms. These bathrooms were gigantic. They were big like the ones on Emirates that have the shower. One of them was, one was bigger than the other. And then tucked myself in, went to sleep, and before I knew it, we were in Frankfurt, and it was over. But what a day. It was amazing.

Alex: You know what? I’m actually surprised you chose this. Not because it is an incredible flight, but that actually was a pretty stressful travel day.

Jess: Oh, that’s when you all like went to the wrong terminal because Pam had booked two flights or something? 

Pam: Yeah. So I guess this, that part could have been my worst travel day.

Alex: No, that wasn’t the worst. We figured it out. We were just running through the airport, but it’s like we scanned in with our boarding passes. My mom’s worked, mine didn’t. And it was like, wait, we booked the same flight. Anyways, we got it all figured out. It worked out. But I, that’s just a testament to how incredible this flight was, because you forgot that the rest of that travel day was a little stressful.

Pam: I really didn’t forget, but it just, who cared? Who cares? This was so amazing. Those six, eight hours were perfection. 

Jess: Well, you were able to tolerate what happened afterwards because you were so well rested, you were so well fed. And you were just like, it’s fine. This is fine.

Pam: Yeah.

Jess: All right, Alex, what about you?

Alex: All right. Okay, so this was kind of hard to choose. I was trying to choose like, okay, something where maybe it’s not like the, because I knew my mom was going to have the best flight. I wasn’t going to be able to top that. Let’s be honest. She’s done the coolest flight of any of us. But I was thinking like, what was a flight where everything just went seamless? Like everything, nothing was stressful. Everything, like connections, everything went really great. And it was kind of hard to choose one. I really loved my Qatar Qsuite home from the Maldives. That was like an incredible, incredible flight.

But I actually decided to go with my flight to Tahiti when I went to Bora Bora the first time. So I flew United Airlines, and this is, I’m going to explain because you’re thinking like, oh, United Polaris, that’s your best travel day? Like, let me just say, I do really like United Polaris.

Pam: Me too. 

Alex: But the reason I liked it so much, I’m going to get into. So first of all, I’m with my mom and my sister to the Conrad Bora Bora. To get there, we had a position to San Francisco and then get to Tahiti. So when we, when booking that flight, my mom, my sister had a ton of United miles because her husband travels a lot for work. So he’s able to rack up a bunch of United miles. My mom, you had a bunch. We found like, I think you used Plus Points to upgrade to business class.

Pam: I did. The one time they’ve worked for me.

Alex: Yeah. So I, though, on the other hand, it was going to be 175,000 points for me to fly business class. I was like, that is disgusting. Like I, not, I’m not going to do that. So those two were in business class, and I was in lowly economy, but I only paid 35,000 miles from Salt Lake City with a, I didn’t even, actually, I didn’t even have to position. My flight went from Salt Lake City to San Francisco to Tahiti.

And so I was like, this is going to really suck. Like I’m going to be in economy, but I only paid 35,000 points, which is a steal to go all the way to Tahiti. I’m going to be in economy, and they’re going to be having the time of their lives in business class. Like I was feeling a little woe is me. I paid like $229 to upgrade to premium economy. Like, it’s expensive to upgrade on a flight like that.

So I was like, okay, at least I’ll, and it’s, it was an actually a daytime flight. So I was like, I’ll be fine. I’ll be in premium economy. Well, that morning, like I had been checking to see what the upgrade offers would be. They were literally to upgrade was $4,000. I’m like, that’s like how much the ticket costs. Like this is insane. So I was like, well, that’s not happening.

I even like checked at check-in, nothing. So that morning, my flight left pretty early from Salt Lake City. So I wake up, I vividly remember I’m in my bathroom, I’m getting ready, and I’m like, you know what? I’m just going to check. I’m just going to check one more time what the upgrade offer is. It was $899, which is not cheap. Like that is still very expensive to pay to upgrade to business class. But I was like, okay, it’s about a nine-hour flight. I think it’s eight hours and 45 minutes from San Francisco to Tahiti.

Jess’s rule is if it’s like around $100 or more per hour in business class. So I was like, okay, it’s a, it’s close. It’s really close. And I was like, my mom and my sister are going to be in business class.

Jess: I gotta be with them.

Alex: This is going to be really sad for me. I’m going to be so depressed if I’m just sitting by myself there. And they’re just going to be having a great old time in business class on this daytime flight. So anyway, I was like, you know what? I’m just going to do it. I was like, I paid 35,000 miles. I’m not paying for anything else like besides my food once I get there, like everything was on points. It was like, you know, this is a trip. This was my justification. This is a trip of a lifetime. This is a bucket list trip. I’ve never been here. I’m just going to do it. And so I did it for the bucket list trip. And I also justified it. Like, tell me this isn’t girl math. I paid $229 for my premium economy seat. Well, they refunded me that money.

Jess: Oh.

Alex: And then I paid the $899. So I’m like, well, I’m actually paying less.

Jess: So you actually paid like $670. It’s like this was basically free.

Alex: Exactly. 

Pam: Girl math.

Alex: So anyway, yep. So I got to go to the Polaris lounge with them when we got to SFO. Like I wouldn’t have been able to go do that. I got on the flight. I like chose a, there was only a couple seats left, but I got one of the ones like on the a window seats. And it was because on United, I forget if it’s even or odd numbers, but one of them, you’re more tucked in, and you have like the armrest on the outside. I had the armrest on the outside. So I was very private. I, it was a daytime flight.

And I don’t know if I’d really flown business class in the daytime, maybe one other time at this point. And it was so fun because here’s the thing, when you fly business class at night. One, it’s hugely important to me so I can arrive well rested. But I’m like paying for that convenience and feeling good when I arrive. And so I don’t really get to, I always like I’ll stay up for dinner. I’ll watch a movie, but in my mind, I’m like, oh, I got to go to sleep. I hope I get enough sleep so I feel good. It’s like that battle with myself of I want to really enjoy the experience, but I also want to not feel like a zombie when I arrive.

And so this time I was like, I just get to enjoy everything. Like I watched the movies. I ate all the food. I had the, I mean, the food’s fine. It wasn’t like groundbreaking or anything. But like the United Polaris bedding is so good. The seat is so comfortable. It was just so fun. And I also had been like, oh, I don’t know. Like, should I have upgraded? Like that was a lot of money. Was that a bad idea?

And then I got on the plane, and I was just like so happy. And it was such a fun flight. And so that for me was one of the best travel days because I just treated myself and I really soaked up the whole experience. It was my first time on Polaris, and I was like, this, this was nice. I got to go to the Polaris lounge, like, got my cookie skillet. It was, it was a really good day. So that, that was my top. And 35,000 points and $899 is pretty good. Pretty good to go from Salt Lake City to Bora or to Tahiti.

Jess: That’s a deal. It’s better than 175,000 points.

Alex: That’s for sure.

Jess: Okay, I actually have two. I just thought of one while you were talking that I didn’t write down. So I’m going to do two, but I’ll make them quick. So the first one, the first one that came to my mind was Emirates First Class flying from…

Alex: Yeah, I saw you choose this one in the notes because this one was amazing as well, because it was also a daytime flight, but I was like, I’m not. So just everybody knows this was one of my favorites too, but I’m letting Jess take it.

Pam: And it was one of my favorites, too.

Jess: So we flew from Milan to JFK. This is unfortunately, I don’t know if I’m ever going to fly this again. It’s gotten a lot harder since I took this flight because none of the banks transfer to Emirates one-to-one anymore. Bilt still does, but I don’t know how much longer that’s going to last. And Emirates really raised the taxes and fees on their award flights. And so it’s going to be tougher.

We paid 87,000 miles for the business class flight from Milan to JFK. And then, you know, I had heard, we have a blog post about this. I had heard about people being able to upgrade to first class at the check-in desk if there was availability. So I forced Ted to get to the airport four hours early, and we went to the check-in desk, asked if there was availability. There was. And so at that point, like I already had my Amex account open, and I was like ready to transfer the miles. And then as soon as she said there was availability, I transferred them. It was 39,000 miles each to upgrade from business to first. I didn’t have to pay any additional taxes.

At the time, we had paid around $200 in taxes. Now they’re more than double that. It’s closer to $475. I still think whatever 87,000 plus 39,000 and $475, I would pay that to fly to take the first class flight again. It’s just harder to get your miles over to Emirates in the first place since none of the banks transfer. It’s going to take more miles.

The biggest reason I wanted to take this flight was because this plane has a shower on it, and you can take a shower in the sky. And I distinctly remember the flight attendant coming around to schedule the time. They schedule you when you want to take your shower. And Ted said, I’m good. I don’t, I don’t want to take a shower. Like, he thinks that’s weird. And I nudged him, and he was like, can I give her my time? So I got two, I think they give you like 20 minutes or something. Um, and so I got…

Alex: But the water runs for like five minutes.

Jess: The water runs for five minutes, and I was taking content and the water ran out. And so in my towel, I had to open the door and be like, can you please add more time? But I mean, the bathroom, the bathroom is humongous. There, they give you like a little bag and all these toiletries to like dry your hair and do your hair and all these like creams and serums and all that stuff I’ve never seen before.

It was a daytime flight, and so that made it really great because we didn’t sleep. I watched, I think that was when I first watched White Lotus. I like watched the entire series of White Lotus. I had my caviar, I had Ted’s caviar. They had like little popcorn buckets that they bring around.

Alex: Ted’s a good guy to travel with. You’re like, I’ll take your caviar. I’ll take your travel or your shower time.

Jess: They brought around, like so, we got to have like popcorn and candy and watch a movie. It was just, it was insane.

Alex: It’s really cute because they do, they have like the popcorn in the little like movie theater bucket. And so you’re just like, oh, I just feel like I’m at the movies. It’s so cute.

Jess: They took a Polaroid picture of us. Like they came around with a Polaroid camera and they took a picture of us, and so we still have it, like with the Emirates sign in the background. So I was like, they are so cute. And it was just a bucket list experience, and it’s the, it’s the flight that ruined Ted forever because after ever since we’ve taken that flight, he’s like, wait, what? We’re flying Southwest again? And I’m like, sorry, we can’t always fly…

Alex: You’re like, that doesn’t exist. You’re like, Ted, this doesn’t exist for domestic flights.

Jess: And then my second one is in July 2022, we flew from Houston to Manchester on Singapore Airlines in business class. RIP that route that no longer exists, but was amazing while it did last. And that was actually the day that I quit my job. So I had given my notice. I was like, I’m quitting.

Alex: What a way to celebrate.

Jess: And it was also my first time ever in business class. And Molly, it was me and Ted and Molly. And so I had never flown business class before. You know, I had been doing this for like seven years at that point. And I was like, okay, $5.60 to fly from Houston to Manchester in business class on Singapore. And it was just wild. I mean, Singapore still, Singapore business, it’s not Emirates first class, but it’s still a great experience. And we get on the plane. I just remember we got on the plane, we sat in our seats, and I look over and Molly is like scrolling through the in-flight entertainment, and she goes, Mom, they have a princess, they have a Queen Elizabeth documentary. And I will never forget that she was so excited to watch the Queen Elizabeth documentary.

Alex: And how old was she? She was like nine?

Jess: She was like eight.

Alex: That’s hilarious.

Jess” We were going, yeah. So we, we flew to Manchester and then went on to Paris from there. But it was just, you know, she got, she got like a thing off the kids’ menu. And so they brought her like chicken and broccoli and peas and carrots on actual serving ware, and like cut up her chicken for her. And I just remember waking up in the middle of the night because I was like, okay, eat your dinner, and then we’re going to go to sleep. I woke up in the middle of the night, and I look over, and she’s just wide awake staring at the screen. Like she is…

Alex: You’re like, okay, well, this idea backfired of her getting rest.

Jess: She has her hands behind her head. She’s leaning back in her in her bed and watching this screen. And I’m like, you need to go to bed.

Alex: She’s like, I got to finish the Elizabeth documentary before we land.

Jess: So that was just cool to like quit my job, hop on business class for the first time ever, and be like, okay, this is my, this is my job now, you know? It was pretty full-circle moment.

Alex: Yeah, for sure.

Jess: Now, let’s go, we’re going to get onto the worst travel day. So Pam, why don’t you kick us off for that one? 

Alex: Womp womp.

Pam: You know, actually, this was kind of a hard question for me because nothing immediately stood out, which is really amazing because I’ve done a lot of travel.

Pam: I’ve had times where…

Alex: I have some that stood out for me for you.

Pam: Oh, did you?

Alex: I’m like, oh, this time was rough for her. But nothing like detrimental, where it’s like your whole trip is ruined.

Pam: Yeah. Yeah. I mean, there’s been some times where I was a little bit nervous, am I going to make that positioning flight is. So there was some times when I’ve been kind of nervous, but obviously all the good experiences I’ve had flying have completely wiped out that bad memory.

But I did think of this one time that was really stressful. My sister and I had gone to Italy. We’d already gone to Rome, and then we, um, and we also did Dublin. No, did we do Rome on this trip? Anyway, we were in Dublin. We were doing it kind of a combination of Dublin and Italy. So we were in Dublin heading to Florence, um, by way of Amsterdam.

And so when we went there to check in, I told her, carry-on only. We’re not waiting for bags. We’re not doing that. You’ve got to fit everything in a carry-on. When we go to check in, and they want to weigh our bags and look at them, and they were too heavy. And sometimes that’s what happens in European destinations. And so I was like, okay, let’s cross our, cross our fingers.

So we got to Amsterdam and our Amsterdam, uh, our flight then to Florence was delayed by about an hour. I mean, I remember we waited and waited in line, and then they got us on a bus, and we, they took us over to the plane. We waited for about an hour standing on that. I mean, it was really annoying. And they said it was all because… 

Alex: Though, oh, those buses are the worst. You were on the bus waiting for an hour?

Pam: Yes. And they said it was all because they were having trouble with weight limits for the baggage and everything on the plane.

Jess: Were you like, it’s my bag, I’m sorry.

Pam: Yes, they were talking about these weight limits. Okay. So finally we get on the plane. The flight was fine. And we get to Florence, and there’s, we’re waiting and waiting and waiting for our luggage to come through. And there’s, it’s just packed in that little, you know, baggage claim area. I think there’s only two little, um, carousels. Yeah, and they’re small. And, you know, nobody’s really speaking much English there. And we’re trying to figure out what is going on. So we were there an hour, even two hours. It was unbelievable. We’re losing our mind. Everybody there that speaks English, we’re all trying to figure this out.

Well, finally, the word comes through that there was no luggage. That they had not put on anybody’s luggage on that flight. And I’m trying to think, uh, we’re waiting around because they’re having weight limit problems. Was the weight limit problems that it was too light because there was no luggage? I mean, how do you not put luggage, any luggage, on a flight and all these delays?

Alex: Well, you’d think that’d be the first thing. Like, oh, we’re having weight limit issues. Let’s check the luggage.

Pam: Yes. No, it was insane. So we wait and wait because nobody really there knows what to do. They have us go get these little papers to fill out. Well, they’ve got three people on this behind this little desk, and you’ve got 200 people trying to get up there, and nobody really speaks much English. It was a nightmare. And we finally got something that someone gave us that, you know, put your information, go online, and put this information in, and we’ll find your luggage for you.

Well, we only had, so we went through to our, um, hotel, we only had two nights there. And I’m telling you, and I love Florence. It’s one of my favorite places. I couldn’t wait to show my sister this. It was a really weird trip. We didn’t see a lot of Florence because we spent half of Florence, of our time in Florence worrying about our luggage, calling about our luggage, searching for our luggage. We did know that they would reimburse some costs because I’ve had this happen to me before, if we need to get some clothes and some, you know, toiletries. So we did do that. So we spent half of our time shopping for stuff that we had in our bags. 

And then, um, from there we were supposed to go over to Cinque Terre. My sister then it get, you know, the whole story gets worse. She finds out that her mother-in-law, who was, had been sick, is dying, and we need to cancel the last part of this trip. But because we’re not going to go because we’re going to go… because we’re not going home, we feel like we cannot leave without our luggage because we had no idea how we ever going to get our luggage. And so we’d filled out papers. We’d called people, nobody gave us any information. We decided this last day, we’re going to go down to Florence Airport. We’re going to find out what’s going on. They did have our luggage. They had a huge room full of luggage.

Jess: I remember you sending us the picture. Like you sent us a picture and we’re like, look at all this luggage.

Pam: No one had contacted us that our luggage was there. I mean, I don’t know when they would have. And so we went in.

Alex: Or how long it had just been sitting there. 

Pam: Just sitting there. So we had to go in there, and luckily we had these fluorescent travel freely tags on. I could find mine easily. Thank you to Zach. Um, so yeah, finally found them. But then, because we needed to leave and we didn’t have our luggage, I had to then, I thought, what are we going to do? I and I thought, let’s just, I’m going to get us to Milan. You know, all roads lead to Milan. We’ll just take a, um, we’ll take a train up to Milan, and on the train to Milan, I booked out how my sister could get home, and I booked out how I could go to London and spend a few days with my daughter there. So it was one of those trips that did not go at all like I planned it to go to.

Jess: See, I thought you were going to say, it’s funny because Alex and I can both think of things like, but what about this one? I thought you were going to say when you flew to Kenya for your safari, and then while you were there, you found out that there were all those floods and you couldn’t do your safari.

Pam: How could I not have said that one? How could I have forgotten that? Yeah.

Jess: But you kind of made the most of it because you ended up…

Pam: Yeah, we still had a really, we ended up going to Sardinia. It was a good trip still.

Jess: But I remember you, I distinctly remember I was in Bora Bora, and you were texting us saying, guys, it’s flooding, we can’t go on the safari. What do I do? And we were like, trying to give you ideas of other places you could go. I distinctly remember that.

Pam: Well, then that reminds me that I also had that horrible day, that the next day from Australia, I’m supposed to go to New Zealand. And while we’re at dinner, someone tells me that they’ve got flash floods in Auckland, New Zealand, and we had to hurry up and I had to change everything that night so that we went to, um, down to Queenstown instead. So yeah, I have had a few days. 

Alex: But you’re really good at pivoting and making the most and turning a mess into like, hey, this was still a great trip. Not what I originally planned, but it worked out.

Jess: And with points and miles, like if you didn’t have points and miles, could you, could you make those pivots?

Pam: No, thank heavens for points and miles. Yeah, it saves the day.

Alex: Yeah.

Pam: And having a stockpile.

Jess: Yeah.

Alex: All right. I’m going to talk about my worst travel day. Knock on wood. Like I literally need to find some wood to knock on. But you know what guys? You guys know that doesn’t work. Knocking on wood doesn’t work. We were just in Costa Rica, and the night before my brother, we were all talking about how no one in our family has had like a major like ACL or, you know, anything like that. My brother said it. And I was like, we need to knock on wood. You guys, the next day we were playing pickleball, and he tore his Achilles when we were playing pickleball in Costa Rica. So knocking on wood doesn’t work.

Jess: You have to do it. I mean, Taylor said that. I ain’t got a knock on wood. All right. Go ahead.

Alex: All right. So, okay, one of our most stressful travel days was when we went to Spain, but I’m not going to talk about that one. Um, we covered it in episode 133. So Jess might touch on it. I don’t know what she’s got planned, but if you want the whole scoop, we talk about it in episode 133.

That was when my positioning flight was delayed so much that it made it so I wasn’t going to make my business class flight to Spain. So I was going Salt Lake City to Dallas and then Dallas to Madrid in business class, and that they were like having storms in Dallas and so everything was delayed. Like, we got on the plane, they walked us off the plane and said, actually, we’re not leaving for a few more hours. So that was extremely stressful, and I wanted to just cancel the whole trip, but I didn’t. I worked it out. Check out episode 133 for the whole story. 

So I’m going to a different one. Uh, this was June 2024. I was flying United Airlines from London to Denver to Salt Lake City. It was Mitch and I. It was after we had gone to Greece and then we spent a couple of days in London visiting my sister and her family. So these were economy flights. We paid 40,000 United miles each and then I think we paid like, I don’t know, we paid a little bit to upgrade to premium economy. Well, we arrived in Denver. It’s like, oh, we’re almost home. Everything’s gone great. It’s been a great travel day.

We’re in Denver. We’d gone through immigration. We’re going through security, like checking back in. And I get a notice like right after we’d gone through, like I’m picking up my backpack off of the security belt. And I get an alert on my phone that our flight has been canceled from Denver to Salt Lake City. Meanwhile, my mom was leaving.

So the plan was like, I would get home, and she was leaving at like, we were going to just kind of cross each other. Or I would get there, and then you were leaving like right after, something like that.

So she’s got to leave. Like she’s got a flight to catch. I think you had another trip you were going on. It wasn’t like you could just be like, oh, don’t worry about it. You guys will get home. I, the kids, like I can stay another night. Like she had a trip she had to get to. Also, in all this, I have one of my kids is sick. He had been throwing up that day.

So it was just like, I just felt extremely stressed. Just like, you know, when you feel like the weight of like a heavy cloud, like weight, like this had been a great trip and then we’re in Denver. We’re literally an hour flight from home, and we’re stuck here. Like, I got to get home to my kids. I, I didn’t feel like I could be like, okay, let’s just call someone over to watch our kids. Meanwhile, my kids sick. Lik,e I don’t want to ask that of somebody. So I was like, okay, I got to get, got to get going on this.

So I go on the United app. I’m first, I’m thinking like, maybe I’ll find a someone at a, you know, a desk to talk to. But then it’s like, everybody on my flight is going to be talking to somebody at a desk. So I was like, I’m get on the United app, and I’m calling them at the same time. And I’m like, whoever can help me first, that’s who I’m going to do.

Well, the people on the chat, I believe it was chat who got to me first. So first of all, I looked on the United app to see because they’ll give you options. If your flight’s canceled, they’ll be like, here’s your other options that you can like get on a new flight. And it’s usually pretty, pretty easy. Well, these flights weren’t leaving till five, six hours later. I was like, I, I got to get home. Like, I can’t leave all my kids home alone.

So I get, and there was another flight leaving soon after mine. That’s the good news. When you’re in Denver, Salt Lake, there’s tons of flights. So I’m like, okay, I’m going to see if I can get on the flight that’s leaving right after mine. It’s leaving in like two hours. Well, that flight is sold out, but I’m on chat with United and they’re like, hey, we can get you on the next on that flight. There’s one seat left, but we can only do one. So I was like, I will take it. Mitch is like, you get that flight, you get home, I’ll figure it out.

So then they’re like, we will put your husband on a Delta flight. And so that to that was like a really key thing to know is if your flight is canceled and the airline can’t get you on a flight, they can book you on a different carrier. Because United couldn’t get us home, they were like, okay, we’ll get you on the Delta flight. So it all worked out, but it was really stressful.

How it worked out is my mom left. We had a car at the airport. My mom left, parked it in short-term parking, hid the key somewhere, I think. And then I got to my car, drove that car home, and then Mitch drove the other car home. So I think my kids were home alone for an hour, but my oldest at the time, he’s old enough. He was old enough to be home with them for a little bit. And so I was like, okay, but I was like so stressed until I got on that plane because that flight that I ended up taking, that other United flight had kept getting delayed too. And I was like, what is happening? It wasn’t, I mean, this is June.

There’s no weather issues. There’s no snow. It was just mechanical stuff, I think. So anyway, made it home, but I was just, it’s kind of that sick feeling where you’re like, I need to get home to my kids, and I, I don’t want to have to like put anybody out to go stay with them overnight or anything. Like, I just want to be home with my kids.

And as I’m sure every parent can relate to that feeling where you’re like, I just need to get home to my kids. This is stressful, and my kid’s sick and he needs his mom. Like the good news was by the time I got home, my kid that wasn’t feeling well, didn’t get, didn’t throw up again, was feeling good. I was like, I made, I made it through without anyone else getting sick. So sorry that you had to deal with the sick kid, Mom.

Pam: Now, was it Kai?

Alex: It was Kai. 

Pam: I thought.

Alex: Yeah. So anyway, that was my really stressful travel day.

Jess: Oof. Okay. I was thinking, so I’m not going to, Ted actually passed out on a Southwest flight coming home from Costa Rica one time, but I won’t talk about that one because I didn’t use points.

Alex: Oh my gosh, I remember that.

Pam: As a former nurse, I have to know why he passed out.

Jess: I think it was because he hadn’t eaten breakfast, and I think it was just something about, like, when we were during takeoff, like the pressure change. I just remember looking, he goes, and like exhaled and then like slumps.

Pam: Oh, how scary.

Jess: I thought he died. I was like, what? So I’m like, ringing the call button. The flight attendants come over, and I was like, my husband, I’m like, Ted, Ted, like shaking him. And I’m like, he’s not responding. Like, I don’t know what’s going on. And so she has to run and get like, they’re they’re paging for like, are there any doctors and nurses on board? And they’re getting like wet cloths to like put on his head and around his neck. And then finally like 30 seconds. You know, it’s like 30 seconds, but it feels like an hour, you know? 

Alex: Three hours. Yeah.

Jess: He’s like, what’s going? And like he had no recollection of wow anything. And like the, it’s funny, like, well, it’s not funny, but the guy sitting behind us was like, I’m a cardiologist, like, so it just happened to be that he was like asking Ted questions. He was like, do you feel this? Like what, you know? And he was fine the rest of the flight. But that was like the scariest travel day, probably.

Pam: Yeah.

Alex: That’s so scary, yeah.

Jess: I won’t talk about Spain because like Alex said, she, we covered it in that episode, 133. My most recent worst travel day is, I think we all have something in common with ours, and it’s like these last-minute cancellations. That’s what really stresses me out because you know, I am a planner. Like it sucks when a flight that you’ve had planned for nine months gets canceled the day before you’re departing, you know?

And so this was when me and three of my girlfriends went to Portugal in October. And we had all, we all live in different parts of the country, but we had found four flights in KLM business class from Chicago to Lisbon on KLM. And so we were really excited because we were like, we’ll all meet in Chicago. It’s kind of central for everyone. We’ll fly KLM, we’ll get our little Delft houses, and we’ll go to Portugal. I think we paid around 60,000 miles for these flights.

So I’m getting on, but we positioned to Chicago. We were going to stay overnight the night before in Chicago. I literally sit down in my seat on the United flight from Houston to Chicago and get a Flighty alert that my flight the next day on KLM is canceled. And I was like, okay, I’m literally like, get going to Chicago. Like I can’t, I have to fly. So…

Alex: Wait, so hold on. I got to ask you really quick. Did the Flighty app tell you before Air France did?

Jess: Yes. And that is what I was going to, in my little section about tips, I was going to say, get the Flighty app. 

Alex: Oh, okay. I won’t… I’ll wait then.

Jess: Get the Flighty app. This is not sponsored in any way, but that app saved me because I got about 15 minute head start on people who don’t have the Flighty app. And basically what I did, um, like we were literally sitting on the tarmac about to take off. I get the alert that the flight is canceled. It’s like, your flight’s canceled, go into the app to like select your new flight. I go into the KLM app, it’s glitching.

So then I decided, I’m going to check the Air France app. I’m able to select a new flight in the Air France app, and it was actually, that was the only direct KLM flight the next day, but there was a direct Air France flight that was going to go like Chicago to Paris to Lisbon instead of Chicago to Amsterdam to Lisbon. And it got me there, I think four hours later than I was supposed to originally arrive, but I was like, it’s fine. So I went, selected that flight.

So that’s the thing, like when you get these alerts, you have to act quickly because everyone else on your canceled flight is going to be trying to get on the same flight as you, you know? And so I was able to quickly go into the Air France app, select the new flight, and from there it was fine.

The nice part is because I arrived more than three hours late, I was able to file an EU261 compensation form, and they paid me like $650 for my trouble. So I was like, hey, I feel like I kind of came out ahead on that deal. But I think it’s just anytime…

Alex: You’re like, do you guys want to cancel my next flight?

Jess: I think it’s just anytime there is a last-minute cancellation like that, it’s stressful, you know? And I looked like, I looked out in that both of these, Portugal and Spain, it was just me. You know, we’ve had really knock, like you said, knock on wood, we’ve had really good luck when traveling with our family. And so it’s a different thing, but like when you’re trying to scramble to get one ticket on the next available flight is totally different than when you’re trying to get four or five or six tickets on the next available flight.

Alex: Yeah.

Jess: So we’ve been really lucky, cross our fingers. But after that happened, I was reading all about how that’s common with KLM to cancel at the last minute. And so now I’m kind of weary to book them. 

Alex: Yeah. Well, and that’s stressful too because you’re like, I’m already on my way to Chicago. Like you’re on the, you can’t hop off the plane, be like, I’ll just reposition somewhere else.

Jess: Or I’ll just fly from Houston. You know, like the only reason we positioned to Chicago was because we found this deal with four seats. And now, if I’m not going on that flight, I don’t really need to go to Chicago, but I’m already in my seat.

Alex: Yeah. Well, and then the other thing was, didn’t your, one of your friends wasn’t able because they were sold out by then and she had to totally rebook a different flight.

Jess: Yeah, she waited a little longer than she probably should have to act on that. And then by the time she did, it was sold out. So she actually arrived a whole day later. All right. 

Alex: So let’s talk about some tips. We’re going to talk about tips for when you have a delayed flight and tips for when you have a canceled flight. So first of all, if you have a delayed flight, we’re going to sing the praises of the Flighty app again. There’s a free version. Jess just convinced me. She’s like, you need to do the paid version. I think it’s what, like $50 a year?

Jess: It’s not very expensive. I mean, I know that subscriptions are annoying. I’m a little burnt out, but Flighty, if you fly regularly, is 100% worth it. Flighty, I pay for Flighty Pro.

Alex: Yeah, I do too. So if you’re flying like once or twice a year, you probably don’t need it. But like if you’re flying often, it can it can really be helpful. Like yesterday, I was flying home, and my flight from Denver to Salt Lake was, once again, Denver to Salt Lake. What’s the deal? No, I’m just kidding. It was delayed because the inbound aircraft, Flighty app told me before anybody else. So, or before United told me.

So if you have a delayed flight, first thing you want to do is monitor the app for changes in flight time. I have heard horror stories where a flight is delayed, and it’s like, oh, we’re leaving an hour later. And people are like, okay, great, I’m going to go to the lounge. I’m going to do this, I’m going to do that. And then the app doesn’t update and tell you like, oh, actually, now we’re leaving at 7:30 because they made up time in the air or something like that. And then they go back, and they’ve missed their flight.

And so the app is supposed to update you again when they make changes, but I’ve heard, and I think it’s very rare, but those stories have stuck with me. So if there’s a delayed flight, I still like, if it’s like if I’m going somewhere from and it’s my originating flight from Salt Lake City, for example. And it’s like, oh, my flight’s delayed an hour and a half. I’m still going to get to the airport at a decent time in case anything changes. 

So I, maybe I’m weird, but I, they always can change it back if they can figure things out. So, um, if you’re going to miss a connection, like as soon as you know you’re going to miss a connection, get on the app and see what you can do. If you’re already at the airport, then you can go talk, like as soon as you get off the plane, go talk to the gate agent. I have heard like the flight attendants can’t do anything. So don’t be, don’t be bothering them with your, I’m going to miss my, all they can do is ask the other people on the plane to sit, stay seated so you can get off earlier. That’s like all that they really can do.

So, um, now, here’s the key part of making sure you’re booking your travel with the right card. So, for the Sapphire Preferred®, for example, we’ll use that one because most people have that one. There’s trip delay reimbursement coverage, but it only starts if your delay is over 12 hours or requires an overnight stay. For the Sapphire Reserve®, it’ll kick in at six hours or if it requires an overnight stay.

So that will cover things like your hotel night, meals, toiletries, medication, other reasonable expenses. And it covers $500 for you, plus any immediate family members are also would get that $500 coverage. So this will cover things like, you know, equipment failure, weather, strikes, anything like that. The key thing here is you got to keep all your receipts. You also want to talk to the airline and get whatever like, you want to get verification from them so that you can submit it to your credit card company. You can’t just be like, oh, so my flight was delayed and this is what happened. Like, you got to have proof of that. So having the right card and the nice thing too is like all you need to do is pay your taxes and fees.

So if you’re booking a domestic flight and it’s $5.60, if you put that on your CSP or your CSR, you’re going to get this coverage. So that’s a nice thing. It is, it would be nice if it kicked in like three or four hours, so you’re able to get yourself a meal. Sometimes the airline will give you vouchers for getting food at the airport as well. So see what you can get from the airline for sure first. And then you might be able to, you know, do some stacking as we like to, as we like our stacks. So those are just a few tips if you’re having a delayed flight.

Alex: So Jess is going to talk a little bit about when your flight gets canceled.

Jess: Yeah. So I covered some of this already, but I think the most important thing to do is act quickly. Don’t think about it. Like, if you have the option to get on the airline’s app and select your own flight next, and you see an option that is maybe it’s not ideal, but it is doable, choose it. Don’t pass go, don’t collect, just do it, right? I mean…

Alex: Do it. Yeah. 

Jess: You’re not going to find, in my experience, it’s like nothing’s going to be as good as the flight you originally booked, but like if you can work with the other option, just do it because you’re going to dilly dally and then someone else is going to take that and you’re going to get an even worse option.

I think if you can do it yourself in the app or if you can chat in the app with someone, that’s going to be way quicker than trying to go stand in line to talk to an agent, along with the other 200 people that are on your flight. And so if you can do it yourself, if you can chat in the app and do it, that is my preference. I always try… 

Alex: One thing I want to say with the app, too, is like in my case, it said the flight was sold out, but it wasn’t. I think it was because we were booked together, Mitch and I, and so there weren’t two seats, but there was one. And so that’s where it’s like you, I say book whatever you can as soon as you can, and then you can always talk to them or chat with them to see if you can find something else.

Jess: And like in Alex’s example, you know, they may put you on a different airline if they have to, you know? And so if you can’t figure it out in the app or the chat, do the app in the chat while you’re standing in the line. And that way, by the time you’re at the front of the line, if you haven’t solved it, someone at the desk can help you.

Typically, as far as like credit card insurance goes, you, the travel insurance doesn’t cover rebooking a new flight. And so if you’re, if you’re on a United flight and it gets canceled and they’re like, okay, here are your options. We can rebook you on these. And you say, no, I’m going to go and pay for my own flight on Delta. Your credit card’s not going to cover that because you had the option to rebook and you chose not to do it. And so I would not bank on getting a refund in that situation.

Alex: Yeah, the only time, like if you get no good options, you can get a refund. Like, the airline is supposed to refund you if nothing works for you. But then at that point, you need to use, you’re still going to have to be required to purchase your own flights to get wherever you need to go, and your credit card company is not going to cover that because they’re going to say, well, you had the options like Jess said, but you didn’t like them. That’s your problem, not ours, kind of thing. 

Jess: And I’m assuming most of the time, a flight that you book on your own very last minute is going to be much more expensive than you paid for your original flight. So if the airline offers something that’s doable, our advice is just take that so that you’re not stuck with a big bill.

Alex: And if it’s terrible, then that’s when you call them or you chat with them and you say, hey, these are the options I got. These aren’t going to work for me. Can you put me on another carrier and see if they can help you out with that.

Pam: Okay. Well, you know what? As we’ve been talking, I thought, you know, all of us travel a lot, a lot more than most people. And yes, we’ve had some annoying times. We’ve had some frustration with cancellations or delays. And it’s never any fun. But, you know, as long as you use the right credit card, as long as you have a plan in place before it happens, it can really set you up to have an experience that’s a lot less stressful. And I feel really lucky that each of us hasn’t had horrendous experiences.

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