What was your worst flight (delay/cancellation) experience for a single trip?
Something brought up for me a memory from a few years ago. I was traveling with my wife, destination of Ixtapa, Mexico. We live close to a feeder airport, no direct flights longer than ~800 miles so we needed actually two connections for this trip. First leg was supposed to go to O'Hare, leaving our airport ~8am. Airline called me at midnight to tell me our flight was canceled due to weather. Spent two hours on the phone and eventually moved everything out 24 hours (including return).
Went to local airport the following day, made it to O'Hare no problem. Then found out our pilot was not there yet - himself delayed on a flight from DC. He was late for our international leg, which brought us too late to Mexico City to catch our final connection. Spent night in Mexico City and ultimately arrived in Ixtapa 36 hours late.
Return was through Houston and Newark. Flight delayed by weather, couldn't catch connection to home spent a night in Newark as well. (continued)