Duke787

Best use was under the old UA award rules and it was my first award redemption after finding FT:

JFK - ICN - NRT (OZ F)
NRT - BKK (TG F A380)
BKK - SYD (TG F 747 - only person in F)
SYD - AKL (NZ Y)
SYD - PEK - NRT (CA J A330)
NRT - IAD (NH F)

160k miles with two 20 hour layovers in Tokyo, a 3 day stopover in Bangkok, and an open jaw AKL // SYD despite flying through Sydney on the way to AKL. Separately had AKL - MEL on EK F on that trip too using AMEX MR and a cheap 12.5k mile upgrade offer from J --> F.

My other best was a last hurrah using US with the girlfriend (unfortunately didn't discover that until they were almost gone). Somehow convinced the US agents that BKK and PEK were the same region so we got charged North Asia/120k price instead of SE Asia/160k price.

RDU - CLT - SFO (US F)
SFO - HKG - PEK (CX F/KA J)
BKK - NRT - JFK (JL J/ JL F)
LGA - RDU (AA F)

Worst is probably spending 50k Aeroplan for 2x SFO - RDU on UA F. It's a long flight TCON for sure (though Eastbound can be less than 5), but I probably could've used those 50k Aeroplan for something better.

knutfin

Best would be using 40000 AA miles on BOM-AUH-LHR on EY F. The coolest part for me was that I earned all of the miles on the BA viking fare (600USD for a tatl trip in J), because of a promo AA had at the time. I'm a student and both J and F is way out of budget, so sitting in an EY apartment felt like the ultimate life hack.

jan_believes

My best experience was when WN oversold a flight and I was on a RR ticket. I bumped and had my discounted value points ticket turned into a voucher that valued my OW fare at over $400 along with the standard $200 for my seat. Used my HH points and cash and booked an Embassy Suites and left next morning. Another passenger split the hotel room with me and I paid less than $30.

My worst? Can't recall.

Tpa-flyer

One of my best redemption experiences came in 2012 when Icelandair ran a purchase miles bonus program and I think it cost about $330 to buy 25K Saga Club miles and the bonus bumped it to 30K. At the time, through Icelandair, I could book a F class seat on Alaska Air from OAK to OGG using those Icelandair miles. As I recall, that F class seat fare was running around $1,300.00 at the time. Both my husband and I participated in the Icelandair opportunity and have wonderful memories of that vacation/flight experience.

hotturnip

My best has to be one of two, both with the old CO (I used to have the easiest time booking awards with them).

I called in March or April to book a flight PIT-VCE in the summer. I figured no chance, but thought I'd call anyway (this was back in 2000). I told the agent where I wanted to go and when, and she just said, "What time of day would you like to fly?" I was stunned.

Also with CO, in 2003, IAH-VIE. I found out in May that there was a once-in-a-lifetime exhibition I had to see in Vienna that ended in July. I called them up, and the agent helpfully found me some dates and a routing that I had enough miles for. I was thrilled.

Worst is every experience with the old US Air. Never had availability for low-mileage awards, and agents were rude, impatient, and condescending (like just about everyone I encountered with US).

If you work for a software company, I'd love an app that would automatically pull award availability from all the airlines, like Orbitz, except with miles instead of prices.

kmandrew

In the mid 90's HNL-DFW was so oversold the AC angel asked if my wife and I would be willing to go HNL-SFO-DFW-OMA; we were on award tickets.- they offered us $1200. The next day I had already booked OMA-SFO for a conference so asked if I could just stay in SFO from HNL and AA refund my OMA-SFO fare. They said yes so we ended up making around $1500.

I have burned 4m AA miles so I'm sure there were some pretty awful redemptions but I always seem to get at least .02 per mile.