I made a huge travel mistake: I trusted the American Airlines app and it cost me dearly

OVERVIEW

American Airlines lost our luggage. Here are three tips to minimize the hassle of mishandled baggage.

• Use AirTags or Similar Trackers: Place Apple AirTags in your checked luggage to track their real-time location, especially in case of mishandling or delays.
• Take Photos of Your Luggage: Photograph your bags (inside and out) before checking them. These images can help identify your bags and streamline the claims process if they go missing.
• Avoid Black Suitcases: Opt for brightly colored or uniquely marked luggage to reduce the risk of mix-ups. If you must use black bags, add distinctive identifiers like colorful straps or duct tape.

Yesterday, my family and flew from Toronto to Philadelphia to L.A. on American Airlines (AA). It was a surprisingly smooth trip … until AA lost our bags and worst of all, wasted my time and that of dozens of other passengers. Here’s what went down:

We arrived at Toronto Pearson International Airport (YYZ) at 9:45am for a 12:33pm flight. Toronto traffic, which is notoriously horrendous, was thankfully clear (the Canadians take their holidays seriously). I’m glad I booked an afternoon flight because YYZ can be a nightmare early in the morning – especially for flights to the U.S. RELATED: Here’s how to beat the madness at Toronto’s Pearson International Airport

Since I have Executive Platinum status on American Airlines, we checked in at the First Class counter but it didn’t matter since there was no line at either. My habit of taking a photo of my bags and double checking the airport codes paid off because this time, I actually needed them to help reunite with my bags.

BTW: If you’re a regular reader of my free daily newsletter, then you know I always recommend traveling with carry-on luggage only since it gives you so much flexibility: You don’t have to show up to the airport so early or stand around for what seems like an eternity at baggage claim or worry about the airline misplacing your bags.

My wife and I used to travel with carry-on only but we now have two little kids (ages five and eight) and on this trip, we were going to a winter destination, so it was pretty much impossible to travel without checking bags. On top of that, we had to help Santa deliver his presents so that only added to the amount of stuff we were packing. Plus, on the return, my wife likes to have enough room to stock up on some of her favorite Canadian treats like ketchup chips. As you can see from the photo above, we checked three large suitcases. In case you’re wondering, the two colorful bags are from ROAM (read our review here and use this link to get $50 off your purchase) and the black one is an Away suitcase.

We don’t normally travel with a black suitcase, opting instead for our brightly colored ROAM bags that no one could possibly mistake for their own.  It’s best not to travel with a black bag since everyone has one and in fact, a woman on our flight to Toronto almost walked off with ours because she thought it was hers. Luckily, I was at baggage claim to prevent the mix up (though her bag wasn’t an Away bag). TIP: If you do travel with a black bag, find a way to make it easily identifiable like using these colorful luggage straps or wrapping some colorful duct tape around the handle.

I must have jinxed myself because the agent looked at me funny for taking a photo of the bag. I said, “I always do this, just in case.” She said something along the lines of, “Don’t worry, we don’t lose bags.” Yeah, right.

On our one hour and three-minute flight to Philadelphia (PHL) I checked the American Airlines app to make sure our bags had been loaded and I did it again while on the PHL-LAX leg of the flight. Both gave me the false assurance that our bags had made it.

It’s funny: After checking the app, I specifically remember thinking to myself that American Airlines and other airlines are remarkable at operations. It can’t be easy to manage almost 6,800 flights a day that travel to nearly 350 destinations in 48 countries. On top of that, managing their tens of thousands of employees, millions of customers and who knows how many bags.

I’ve checked bags a lot and American has only lost them a handful of times. But my goodwill towards AA quickly ran dry after about 30 minutes at LAX’s baggage claim. I stood around and watched as some of my fellow passengers got their bags and then the carousel stopped with dozens of other passengers still standing around.

I immediately went to the baggage desk since there was no line yet and asked what was going on. The agent looked up my bag using my last name and said, “Yeah, your three bags are on the way. Just be patient.”
After 30 more minutes, there was still no sign of our bags so I went back to the baggage desk. This time, the line was long. Fortunately, one of the reps made an announcement specifically for the Philly passengers on AA flight 1799 that they were aware of the problem and asking everyone to just be patient.

Since our ride had been waiting all this time for us, I escorted my wife and kids to the car and asked them to take them home and I would make my own way home. This was the only smart move I made of the night because 30 minutes later, the agents made another announcement for Philly passengers to come to the baggage line.

By now, the line was way too long and the agent told everyone to scan the QR code on the counter (see above), tap the middle option and fill out the form (bag tag or flight confirmation number, description of bag and a long list of potential contents). Once completed, American would deliver your bags within a 50-mile radius the following day for free.

I figured the plane’s cargo door was broken and they couldn’t open it, which is understandable, but I was told, “No, the bags weren’t loaded on the plane.” But, I said, the app says they were. Another passenger said the same: “Yeah, mine said my bag was loaded twice.” Turns out mine did too, which should have been a red flag.

At this point, I was kicking myself for not having my wife near me, even though she was exhausted, because she had the AirTags on her account and hadn’t shared the location with me. They were new AirTags. BTW: They’re currently still on sale so now’s the time to buy before the price goes up, likely in the new year. Buy Apple AirTags here.

Trying to fill out the form while walking to the end of the airport to catch a ride to avoid what was now the evening crush, wasn’t fun. I can’t believe AA asked for contents and had about 40 options. Like I have time to list everything so I just checked “shirt.” Note to self: Next time, take a photo of the inside of the bags. Unfortunately, there was no place to upload a photo so I contacted AA via X, with a DM and the photo. They helped escalate it.

When I finally got hold of my wife (she was already home and getting the kids ready for bed) and asked her to check the location of the AirTags, I could feel her jaw drop through the phone. She checked her Find My app and said, “Umm, they’re 2,400 miles away in Philadelphia!” Ugh.

If I’d only checked the AirTags when we landed, I could have saved so much time and aggravation. I was irritated at myself and at American for giving us (especially seniors and those passengers with babies) wrong information.

It’s been 24 hours and according to AA’s tracker and our Apple AirTags, all three of our bags are in L.A. and were picked up from the airport about an hour ago but they have yet to be delivered. To make matters worse, we were supposed to fly to Honolulu tomorrow on their seasonal 787 in First Class. I was able to use four, soon-to-be-expiring System Wide Upgrades but those lie-flat seats are going to be filled by four others because we’re not going. My wife has gotten sicker and we have no bags. Update: Our bags arrived just after 9pm so it took 27 hours for them to be reunited with us. And this was from two of American Airlines’ hubs (PHL and LAX) so if your bags were left at an airport without a lot of frequency, expect it to take longer.

We were on the fence about the trip now that Natalie and Olivia are sick and then I got into my first ever (and hopefully last) car accident this morning after returning home from the grocery store. A nice mother of two young children (who were home sick with the flu after a trip to Hawaii themselves), plowed into me while I was stopped at a red light. I didn’t see it coming and it really shook me. I couldn’t believe how loud the sound of the crash was. The cops came and she admitted that she was at fault (she was driving her husband’s car, had flip flops on and said her foot slipped.) I’m pretty shaken up and already feel some pain, which the cops warned me could worsen by tomorrow. I guess it’s true … when it rains, it pours.

I can’t help thinking: If our bags had come out when they were supposed to, or if we had used Ship & Play, a luggage delivery service, like my wife originally wanted to (they were offering us a free-trial), or if American Airlines had told me the bags hadn’t made it or if I had checked the location of our AirTags immediately, the accident would never have happened since I would have gone to the grocery store right when we got home, as I usually do.

But I guess it’s all about timing. Life has a funny way of throwing curveballs when you least expect them, but sometimes, you just have to roll with the punches—and hope the next trip is a little smoother and smarter (use AirTags!)

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