Spent 280K QF miles for OW Award for 2 people on following routes last year:

Y CX SYD-HKG
Y CX HKG-LHR
Y AY LHR-HEL
Y AY HEL-ZRH
Y CX AMS-HKG
Y CX HKG-SYD

Paid about A$750 tax per person. Ironically, CX had a sale where SYD-HKG-LHR return was only A$1300 per person. So I throw away about 200K away for about A$1200 (if still using points for redemptions on intra Europe flights). I protested but my better half won't budge.

That cant be the worst use of miles, that must be the best use of the miles!

Upgraded from Y to First on BA. Should have just upgraded to club.

Spent 100,000 PanAm WordPass points to take a girl from BAH-JFK for one night, ostensibly to see a broadway show. I don't remember the show. I remember the girl.

Worst? I don't know but it certainly was the most ostentatious.

100k miles
2x F awards
DFW-LAX

on MD80s

morning flights (no alcohol service)

It took me 14 years to earn those miles. Two months later, I discovered Lucky's blog then flyertalk and have earned about 300k miles with my new found knowledge.

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.