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Winning The Frequent Flier Lottery

by Jason Steele

I am a very jaded traveler. In the airline business, my only loyalty is to the company that is offering the most miles at the least cost. The other side of the equation, the redemption, is where I have the most problems, like everyone else. My standard advice is that frequent flier programs are like an unregulated lottery. That is mostly true, but not always. Typically, what you will read in the travel column of  any major newspaper or magazine is the same old generic advice. Plan your trip in advance. Be flexible with the dates. Consider utilizing an alternative airport. By now these tips are about as useful as a baseball coach that insists that the key to winning is to score more points than the other team.

Jason Scores Thanksgiving

In the world of airlines, Thanksgiving is like the Super Bowl. Sure, Christmas is a busy travel time, but most families enjoy more generous breaks from school or work, allowing them to spread their travel across a few weeks rather than compress it into a single, long weekend. This gives them date flexibility and allows them to consider driving. Don’t forget that Christmas is mostly celebrated by Christians, unlike Thanksgiving which everyone wants to be a part of.

This year, like most, my family had resigned to the fact that it just wasn’t practical to travel to see the rest of the extended family in Atlanta. Sure, Southwest was flying to Atlanta, giving me some hope of using miles on a holiday, but their service only starts up next February. Frankly, I hadn’t bothered to look for frequent flier awards on other airlines as it just seemed impossible. Then something unusual happened yesterday. My wife was confirming someone else’s business class international award flights and was told that first class had opened up on a domestic segment that they were only able to get in economy. On a whim, I checked flights on United between Denver and Atlanta during Thanksgiving weekend. I was stunned to find some availability at the lower redemption levels.  Before long, we had three first class tickets arriving and departing not too far off of the flights I would have booked if I had my first choice.

What is truly mind boggling is that one of the aircraft is a regional jet, equipped with only six first class seats. Like some Saudi prince traveling with his entourage. our family just booked half the first class seats on a single flight!

The Downsides

One could argue that paying 50,000 miles for a 3.5 hour domestic flight is not a very good use of miles. I probably would have joined that argument a year or two ago. Obviously, I came to a separate conclusion this week. Miles are there to be used, not saved for some rainy day. Despite the relatively short flight, this is still a ticket that would have cost about $400 in coach. The fact is that I am somewhat miles rich and time poor, as 2/3ds of our family is currently enrolled in school. This cuts down our family travel time to school breaks and such. Simply put, if I didn’t use these miles for this trip, I really didn’t have any other plans for them.


Spending miles at the lower mileage rates is much harder than earning them. Somehow, my family won the lottery this year, scoring seats on the busiest travel days of  the year. Perhaps there aren’t many business travelers that week expected to purchase first class seats, or maybe other travelers, like me, simply assumed that they would never find award seats on Thanksgiving. Either way, this will be an award long remembered, as each year will probably re-tell the tale of the time that I found three award seats, two months before Thanksgiving.

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