Over christmas 2005 I was delayed for 5 days on the same flight!
First flight on a Tuesday afternoon was delayed for weather, would have missed my connection, had to resched the next day stand by...
Ended up doing stand by for the 2nd and 3rd day with no openings.
On the 4th day I had a seat, but the flight got cancelled. No rebookings that day.
On the 5th day I finally got on the plane, we took off, and ended up circling over ORD for 1.5 hours.
Missed a connection in ORD and got a later flight, ended up back home in the early morning hours of the 6th day!

The original flight costs $225 or so, by the time I got home and done, I had collected almost $1400 worth of flight vouchers!
Total insanity!
Where was the delay? MKE to ORD
I couldn't drive it and pick in ORD because I had an infant with me and no car seat. No bus or shuttle had car seats available so I couldn't even make it down there.
ahhh the joys of children.