The Worst Flights Upgraded Points Team Members Took in 2025

Not every flight is a winner. Sometimes, things go wrong — think delays, lost luggage, or grumpy flight attendants. There’s also the opportunity for sweating inside the plane mixed in.

While we took some incredible flights this year that were memorable for all the right reasons, the flights our team details below were memorable for the bad experiences they provided.

Ryan Smith, News Managing Editor

I didn’t know this was my worst flight until after it ended. At check-in, in the lounge, and while I was in the air, it seemed like a good flight. Then, after I landed, my first time flying with Virgin Atlantic fell apart.

I was very excited to fly Virgin Atlantic Upper Class (the airline’s business class) for the first time, paying a dirt-cheap 29,000 Virgin Points to fly Upper Class from New York City (JFK) to London (LHR). From London, I connected onward to Barcelona (BCN) on a separate ticket with a different airline.

Incredibly, Virgin Atlantic never loaded my suitcase on the plane at New York’s JFK airport. At London Heathrow (LHR), I filled out all the paperwork for missing luggage and was told the suitcase was still in New York; the desk agent was by no means friendly, but he was efficient. He promised — in no uncertain terms — the bag would be delivered to me within 24 to 48 hours, brought to my home in Barcelona.

Yeah … I wish.

The ensuing process had numerous headaches. I asked this gentleman how to get in touch with Virgin Atlantic, given that the airline doesn’t serve Barcelona and I’d likely have questions. He directed me to contact the airline on X (formerly Twitter) … and linked me to a spoof Virgin Atlantic account.

This put me in contact with a spoof third-party agency that interrupted me, talked over me, and consistently raised their voices when talking to me on the phone. On one particular day, they kept calling me while I was in a meeting. They called 7 times in a row, rather than just leaving a message.

On another occasion, this agency advised me to create an account with WorldRemit as a payment platform to receive compensation for the ongoing delays. While on the phone with them, the agent said he would create the account for me and was sending me a one-time passcode. First, that sounds suspicious already. Second, when a text message from a financial app arrives saying “Do not share this code with anyone,” you can bet I’m not going to read it to you over the phone.

The agent became belligerent after I refused to share the code with him.

Hot Tip:

If you receive verification codes from your bank, loyalty rewards account, or another agency that you weren’t expecting and someone calls you asking for the code, assume it’s a scam. Don’t give the code to someone you don’t trust implicitly.

Communication with the real Virgin Atlantic, which came via email, was confusing. My bag was in Barcelona, still in New York, and permanently lost — and sometimes it was all of those in the same day, according to the notifications I received.

Plus, since Virgin Atlantic doesn’t fly to Barcelona’s airport, the promise that my suitcase would be delivered to my home was broken. It turns out the airline doesn’t have any agreements with any agencies locally, and my bag went to the airport’s general lost and found office. I had to go retrieve it at the airport, which is an hour each way for me.

It took over a week to get my suitcase, I was shouted at on the phone, the entire thing felt like someone was trying to steal my identity — something I was right to be suspicious about, now that I know I was in touch with a fictitious Virgin account.

The flight itself was good, but how do I forget this experience? I’m not sure I will.

Tiffany Eastham, Director of Compliance

For me, the title for the worst flight of 2025 goes to Aeromexico on my journey home from Mexico City (MEX) to Vancouver (YVR).

It was an unbearably steamy day in the low 90s, and with a boarding time of 4 p.m., the sun was at its peak.

Despite a great time in the Centurion Lounge beforehand, the terminal itself was already quite warm and stuffy. But upon boarding the plane, it was even more stifling — not surprising for a metal tube that had been sitting on the blazing tarmac for who knows how long.

As passengers continued to file in, there was no relief from the heat. People in the rows ahead constantly reached up to open the vents, but nothing but hot, stagnant air wafted down.

As the heat continued to intensify, “boarding complete” was announced over the intercom, yet we continued to sit for another 45 minutes without any update or any temperature control (or any empathy or response from the crew).

Every bald head in front of me was soon glistening with beads of sweat. Passengers would stand — backs completely soaked — in an effort to grab some shorts out of their bags in the overhead bins. Even the woman seated next to me stripped off her shirt in one swift movement — no hesitation, no shame.

At this point, I was sweating through my jeans. Yes, I admit that wearing jeans on this travel day was my first mistake. Wearing a light grey shirt was my second.

When an older woman passed out in the aisle, and medical personnel had to be called, I knew it was dire. Even I was starting to feel panicked from the suffocating heat and claustrophobia.

After more than an hour of slow-roasting from the inside out, we finally pushed back from the gate, but the cold air didn’t start flowing until we reached cruising altitude some 30 minutes later.

And there is no stranger feeling than going from fighting off heatstroke to battling a full-body shiver, fully soaked in your own sweat, and plastered to a leather seat. It was the longest, stickiest, and stinkiest 5-hour flight of my life.

Gracias, Aeroméxico.

Nick Ellis, Senior Editor and Content Contributor

The worst flight I took this year began in an exceedingly normal manner. It was a domestic flight, operated by United Airlines, from San Francisco (SFO) to Chicago (ORD), after a fun weekend of visiting friends in the Bay Area.

I was traveling with the carry-on suitcase I’d had for 10 years at the time, and it had traveled around the world with me many times — almost exclusively in the overhead bin (except for regional jets).

Everything was proceeding smoothly until it was time to board. I have no elite status with United, and I was assigned boarding group 3. I had chosen my seat ahead of time and knew I was sitting toward the back of the Boeing 757 aircraft.

I was slightly concerned that the plane would run out of overhead bin space, but then I remembered that because I was in group 3, the vast majority of the people boarding before me would be toward the front end of the plane, as groups 1 and 2 are mainly comprised of first class and United’s top elite flyers.

When it was my turn to get on the plane, I scanned my boarding pass, and then I was stopped by a gate agent who told me my bag wouldn’t fit inside the overhead bin. I calmly explained that I’d had my bag for a decade and that it fits in every mainline aircraft overhead bin I’ve ever traveled on.

He responded by telling me that this plane — again, a Boeing 757 — was an older aircraft type and that the bins were much smaller than what I’m used to. I told him that I’ve flown on dozens of flights on 757s (and even that it’s one of my favorite aircraft!), and the fact that I’d flown a 757 out to San Francisco and had no issue, but he didn’t believe me.

At that point, the rationale for not allowing my bag on board turned to the possibility that there wouldn’t be bin space at all. I tried to explain that I was boarding in group 3, but sitting near the back, so there’d be a good chance that there’d be plenty of space for my bag. He refused to acknowledge my reasoning, hurriedly handed me a gate check tag, instructed his colleague to take the bag from me, and said that I could pick it up at baggage claim in Chicago.

This was exactly the situation I was trying to avoid. It was an evening flight from San Francisco, meaning I was landing in Chicago late at night on a Sunday, and the last thing I wanted to do was snake my way to baggage claim and wait for my bag to come out — which can take quite a long time at O’Hare.

Ultimately, there was nothing I could do, and I wasn’t going to escalate the situation with the gate agent. Still, I was frustrated, especially as someone who has flown hundreds of thousands of miles over the years, by the fact that all of my reasoning and experience were essentially null and void.

Of course, by the time I reached my seat, my hypothesis had been confirmed. There were barely any passengers in my area when I boarded, and several overhead bins directly in my vicinity were completely open.

The flight itself was completely fine, and there were no issues to report. But the experience at the gate left me with a bad taste in my mouth, and I’ll admit that I was still salty about the entire ordeal when I was weaving my way through the endless halls of O’Hare to get to baggage claim.

Chris Hassan, Social Media and Brand Manager

I’ve had my fair share of delayed and canceled flights this year. According to Flighty, I’ve lost 35 hours to delays in 2025 alone — not great!

However, there is 1 flight that stands out the most, and it happened to be from the same airport on the same night as Ryan’s worst flight. (We met up to chat for a while, which was fun.)

I was due to fly Delta from New York (JFK) to Burlington (BTV), but it ended up being a JFK to JFK flight, which was a first for me.

After rolling delays due to weather, the government shutdown, and maintenance issues, I finally boarded my flight to Vermont around 8 p.m. — 5 hours later than initially scheduled.

I was in good spirits, sitting in first class, enjoying a cocktail as we taxied onto the busy runway. Being number 20 in line for takeoff, I was worried our crew would time out, but we took off without issue and were on our way to The Green Mountain State.

About 1 hour and 45 minutes into the flight, I was curious as to why we hadn’t started our descent yet, only for the pilot to announce that we were heading back to New York. The reason was that the deicer in Burlington wasn’t working properly, and since it was snowing, they couldn’t risk getting stuck.

When we landed back at JFK, the crew announced that the flight had been canceled and instructed passengers to head to customer service for rebooking options. I knew there was 1 flight left that night, so I booked it while deplaning — and good thing, since the customer service line was 20 people-deep.

A wise Delta agent told me to go to a different terminal, as I might have better luck, so that is what I did. Meanwhile, my wife (at home in Brazil) was on the phone with Delta while simultaneously trying to rebook me via the app. Just as I made it to the next terminal, my wife confirmed me into the last economy seat on the final flight of the day to Burlington — a downgrade I happily accepted.

After returning to my original terminal, I boarded an uneventful flight up to Burlington for a quick visit with my grandmother … only to find out that my luggage stayed behind in New York and wouldn’t be delivered for another 2 days.

All said and done, I got where I needed to be, though later than expected, and I was able to do a little shopping on Delta’s dime. I’m just glad I was solo on this trip, rather than having my wife and kids in tow.

Final Thoughts

From baking inside the plane to lost luggage and bad staff, we had some interesting experiences that amounted to our worst flights this year.

The good news, though, is that we all arrived safely at our destinations (even if a bit late), and the best news is that most of our flights this year were excellent.