A U.S. traveler recently found an unexpected ally in ChatGPT after a medical emergency forced him to cancel his dream vacation to Medellín, Colombia. Facing a non-refundable $2,500 loss, he turned to artificial intelligence for help—and it worked.
In a now-viral Reddit post, the traveler explained that he had booked a flight and hotel through Expedia, both of which had strict no-cancellation policies. “The hotel had a no-cancellation policy. The airline had a no-cancellation policy as well. I asked—and they both absolutely said no,” he wrote.
Without travel insurance and with no other options, the traveler sought assistance from ChatGPT, asking the AI to advocate on his behalf. Although his initial appeals were rejected, the traveler decided to cite a legitimate medical condition—Generalized Anxiety Disorder (GAD)—and backed it up with a doctor’s note. He then asked ChatGPT to help him write a formal appeal referencing the policies of Expedia, the hotel, and the airline while explaining his medical situation.
The result? The hotel agreed to refund his booking. However, the airline was more difficult. Their policy only allowed exceptions for terminal illness or death. GAD did not meet that criteria, but ChatGPT crafted another letter for him, explaining how his condition could affect his flight. Within an hour, the airline reversed its decision and issued a full refund.
The story quickly gained attention on Reddit, where many users praised the traveler’s persistence and the effectiveness of AI. One commenter remarked: “ChatGPT might have just paid for itself a hundred times over in one shot.” Others echoed similar sentiments, calling it a reminder to not take “no” for an answer.
However, not everyone was impressed. One user criticized the traveler’s approach, questioning its ethics: “Congratulations. It’s because of people like you that cause companies to treat customers poorly. So you lie to get something you’re not entitled to receive.” The traveler responded, clarifying that ChatGPT had not fabricated anything but helped structure his real medical condition into a more compelling argument. “Had I not used ChatGPT,” he explained, “I would have had to hire a paralegal—and that would’ve cost me more money.”
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