We booked flights through CheapOair and even paid for travel insurance believing it would protect us if an unexpected life situation occurred. Unfortunately, our circumstances changed in the most difficult way possible. My sister is terminally ill and has been given only 30–60 days to live. The flight we had booked happened to fall directly on her birthday, and I simply could not justify being away traveling when there is a very real possibility that it could be the last birthday she ever has. We made the decision to cancel our travel so that we could remain with family during this extremely difficult time. What followed has been one of the most frustrating and exhausting customer service experiences we have ever dealt with. For the past several days we have spent hours on the phone being bounced back and forth between CheapOair, the airline, and the insurance company. The airline tells us we must deal with the third-party agency that sold the ticket. CheapOair tells us to call the insurance company. The insurance company then sends us back to the airline or CheapOair again. This cycle repeated itself for three to four straight days with no one willing to actually take responsibility for resolving the issue. Every call ends with the same scripted responses and no real effort to help. The most upsetting part of this entire experience is that the only solution we have repeatedly been offered is that we must provide medical records from my dying sister in order to receive any consideration for a claim or credit. I will never ask a terminally ill family member to produce private medical documentation simply so we can recover the cost of a cancelled flight. It is unreasonable, insensitive, and frankly inhumane to expect a family to chase down medical records while dealing with the emotional reality of a loved one nearing the end of their life. What makes this even more frustrating is that we are not even demanding a full refund. We simply asked for a reasonable credit that could be used toward future travel once our lives settle down after this incredibly difficult period. Instead of compassion or flexibility, we have been met with rigid policies, repeated scripted answers, and a complete lack of understanding for what families go through when someone they love is dying. Travel insurance is supposed to provide peace of mind when life takes an unexpected turn. In this case it has provided nothing but stress, frustration, and hours of being sent in circles between companies that all seem unwilling to help. The entire situation has felt like a system designed to exhaust customers rather than support them when they actually need help. We have already filed a complaint with the Better Business Bureau and escalated the issue to CheapOair's corporate offices because normal customer service channels have not provided any meaningful resolution. We are still hopeful that someone in a position of authority within the company will review this situation with basic compassion and fairness and provide a reasonable solution such as a future travel credit. Until then, our experience with CheapOair has been extremely disappointing and one that we would not wish on anyone dealing with a serious family crisis.