qbrain is the winner so far. I've blocked my equivalents from my memory; they're too painful.

15k miles on UA to upgrade on an EMB 170 IAD->MCI to watch coworkers do the walk of shame to Y.

This was back in my younger years.

2x 45K AA miles J awards for my parents
HKG-PEK on KA return

Thank god I'm earning them at a good rate lately!

I am pressed to say my worst use will be 75,000 AAmiles for round-trip ORD-LHR-JNB in back of the bus (my legs already hurt), for a flight that usually costs about $1200.

However, since it's for this summer's World Cup, I think I'll leave it off my worst list for now. Unless of course the USA goes 3-and-out. Perhaps I can use even more miles to extend my stay for a Quarterfinals run :)

So I guess my worst was actually 45,000 for a round-trip in F on AA from ORD-MIA (both early morning flights). Was during Thanksgiving week so again, can't really complain.

I have to admit the night was more than worth the miles spent - I was more less referring to the actual amount and distance flown :cool:

I burned 75k of miles (all I had at the time) for 3 DFW-LAX RT because I was worried about cash. Ticket prices at that time were $259 AI. 4mo later ticket prices were $350+ and I was out of miles and paying cash :-P

Ouch. At least the girl was memorable.

I think I cashed in my 20,000 chase points for less than half a cent a little while ago, that was probably wasn't too smart.