The Biggest Customer Service Fails I’ve Experienced in Travel

Louie CK has a hilarious skit where he compares fliers describing their harrowing journeys akin to surviving the Oregon Trail.

From epic delays to lost luggage to missed connections, whoever said, “Enjoy the journey, as much as the destination” clearly never had a layover at ORD. Everyone who’s ever traveled has travel fails or two about getting there. Here are some of mine.

Dollar Rental Cars

Dear old Dollar, whose tagline is, “We never forget whose dollar it is” forgot whose dollar it was. I returned a car an hour late expecting a small hourly fee to be tacked on to my bill. Not stopping to check the total, I got home and found a $500+ charge on my credit card. Thinking it must be a mistake, I called their customer service number only to be rudely told that if you return the car after your allotted time, it completely voids your contract giving them free reign to change your rates as they see fit. Somehow they decided to jack ours from $35/day to $99/day. After a series of hilarious mean tweets later including a poll to my audience they sincerely regretted that decision and reversed the charges. Buyer beware.

Enterprise Rental Cars

With a motto of, “We’ll pick you up,” you’d think Enterprise would go above and beyond to make the car rental experience easy. Well they do, until they decide to sell the car you’re driving. Apparently, Enterprise (and a few other rental car companies as I’ve learned), have a whole separate division setup to sell their used cars that doesn’t communicate with rental operations to know what’s in-stock and what’s unavailable. And if that car you happen to have rented is bought while you’re driving it – you’re SOL. They need you to return it ASAP, no matter where you are or what you’re doing. It was a huge inconvenience to have to drive the car all the way back from the city to the suburbs where I rented it, completely disrupting my vacation without so much as a thank you or sorry it won’t happen again. Sure, I got an upgrade when I returned it, but the replacement car came with a completely empty gas tank, which they didn’t bother to check when they threw the new keys in my hand. Not only did I have to make one unnecessary stop to return the car, I then to make a second stop to get gas. Serious customer service #fail.

Budget Rental Cars

Apparently, I’m on a roll with rental cars. Another Thanksgiving travel fail, which seems to be a trend (it is the busiest travel day of the year), we rolled up to the rental counter only to find Budget had run out of cars and would not be honoring our reservation. The options they gave us were take a Texas-sized pickup truck (to park in downtown Chicago, no thanks) or try out an EV. I’ve never driven an electric vehicle in my life but let me tell you, I never will again. We spent half the trip looking for chargers and the other half wasting time in parking lots waiting to charge, which in Illinois is apparently like the Hunger Games. In Rockford where my parents live, the options for charing stations were the brewery (encourage drinking and driving much?) or a cancer treatment center. What we learned was all charging ports are not compatible with all cars and “fast” charging still take an hour, while “slow” chargers take 6-8 hours. I would like those hours of my life back.

Atlanta Airport

One of the weirdest travel experiences I’ve ever had, my whole family was stuck at ATL when they claimed a fire shut down all the power, knocking out the generator and the backup generator. Somehow, it didn’t even make the news that no flights were taking off so people kept showing up and were not being let out. I have my theories what really happened, but their lack of communication left thousands of people stranded during one of the busiest travel times of the year and was a complete cluster. I’ve also seen some things on the plane train…but that’s a story for another day.

Air Berlin

Oh Air Berlin. Worse than Ryanair in my eyes, during a three-week romp through Europe, after of course charging me to check my bag, they lost it. “Don’t worry,” everyone said. This happens with all discount carriers. “They’ll find it, and it’ll be delivered to you in your next city.” Wrong. My clothes and all the souvenirs I’d acquired after being gone nearly a month were never recovered. Washing their hands of any responsibility and failing to communicate any action aside from a few “out of office” emails in German, they simply told me to file a claim with my insurance carrier. Like any good Jew, I threatened to sue. Going back and forth and harassing the sh*t out of them for weeks, they finally transferred a measly $300 into my bank account. This being the second time I’d completely lost my checked luggage (the first was on American Airlines, who without any fight gave me over 3k to replace everything for a mere week-long trip), I have learned to take nothing but a carry-on that doesn’t leave my sight.

Frontier Airlines

Sensing a theme here? Flying can be stressful, sometimes even before you get to the airport. Super excited I found a reasonably priced ticket to SXSW, I was willing to brave Frontier despite the horror stories I’d heard since being taken over by Spirit’s CEO. Skyscanner is one of my secret weapons to always finding low fares, and this is the only time they’ve ever let me down. I booked my ticket, my credit card was charged and I received my confirmation email. All seemed fine and dandy. About a week before I was supposed to fly, I realized I never had a seat assignment. I tried to select one on Frontier’s website, but I kept getting an error message that my confirmation number was not valid. Frustrated, I called their 1-800 number, which did not even give me the option to speak to a person. It was just an automated message, “We’re experiencing high call volumes, if you’re not flying within the next 48 hours, call back and try again.” Click. There was nowhere to even leave a message. I’m not sure how you were supposed to be connected to anyone if it was an actual emergency. Needless to say, emailing them was just as futile. Apparently my ticket had never been issued, despite being confirmed. They accepted no responsibility and insisted I had to rebook, despite being a week out and fares being over $200 more.

An Airline I’d Like to Remain Nameless

This is probably my favorite travel story of all time because it’s just so ridiculous that years later I barely believe it even happened. Flying home from college for Thanksgiving one year, it’s not unusual to be delayed for weather as both Colorado and Chicago are snowy destinations. After taking off three hours late, everything seemed to be going according to plan. That is, until we landed. Once on the tarmac, an announcement came over the loudspeaker. “We’ve reached our destination, but while we were in flight, the crew decided to go on strike so we physically cannot let you off the plane until we reach an agreement with management.” Yes, a plane full of people were essentially being held hostage and used as bargaining chips for the union. You can imagine the mood on that plane. After being delayed a total of eight hours (three for weather, two in-air, three while we sat helplessly awaiting negotiations), I got a lot of frequent flier miles for that one.

Travel Fails are Part of the Experience… How You Handle Them is Up to You

Travel, like life, is a chaotic improv show with no dress rehearsal—and sometimes the supporting cast drops the ball spectacularly. Whether it’s a hotel that ghosts harder than your Hinge date or an airline that redefines the word “inconvenience,” one thing’s for sure: no one’s immune to a good ol’ customer service fail.

But as frustrating as these moments are, they make for killer stories and hardened travel instincts. Now I book smarter, pack lighter, and carry an Olympic-level eye roll just in case. Because while I may forgive (eventually), I never forget—and I always let them know so they can improve.

Here’s to fewer disasters and more delightful detours. And if the travel gods throw shade again? At least it’ll make great content. Anything like this ever happen to you? Let’s hear the tales!