a man taking a selfie in an airport
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A Points & Miles FAIL.

It’s so easy to give out advice, but a lot harder to take it. Today I come to you, hat in hand to admit that I lost. I played a game of points and miles roulette, which many points enthusiasts and last minute hopefuls have played before – and I lost real money and probably future hair for doing so. Here’s the saga, the lessons and everything else to be learned for others (and myself). And to be fair, I am still writing this from a first class lounge and will make it to my destination on time – so it could be worse.

a city with a church and buildingsThe Backstory

I’m on my way to Southeast Asia with my wife Laura, for the usual mix of business and pleasure. We’re currently in London and a flight from London would’ve made perfect sense, but we’ve been wanting to fly a Finnair A350 on a nice, long flight, for a good while. We booked our Bangkok flight from Helsinki, using points, just a few weeks ago, assuming an easy flight option from London to Helsinki, Finland would present itself. Unfortunately, the next day, Trump and Putin announced their Helsinki summit for the coming days of July, and flight prices quickly jumped – and points availability disappeared. Our onward flight from Helsinki is tomorrow, and given the timing and a moving landscape, the only safe option (many flights tomorrow are already sold out) was to fly out of London – tonight.

A Great Strategy

Points and miles can be a game of roulette. Some flights are more expensive than you want to pay for, and waiting for last minute availability to pop up can be an absolute godsend for the wallet. As a generally above average points & miles player, I began checking for definable patterns in Finnair set availability using points over a week ago. I’d planned to use 7,500 Avios points to cover the otherwise expensive flights, and began searching on each and every day to see how availability was shifting – and if any patterns regarding releasing seats could be learned. I quickly learned that between noon and 2PM each day, Finnair seemed to be releasing all the remaining seats for their evening flight for points availability. Less than an hour from Heathrow, this seemed to be the perfect option. I watched this happen for six consecutive days, which gave me great confidence that the same would happen today, when I needed to get to Helsinki.

a white airplane in the skyA Great Failure

I rolled the dice, quite sure that my points roulette would pay off, as it has done so many times, and that my wife and I would dodge yet another expensive fare by playing the waiting game. But with Trump landing in London, Thursday night business traffic and the impending Helsinki summit, no seats using points were ever released. In fact, it became readily apparent that if we didn’t book a seat on any available flight this evening, we may not make it to our onward Helsinki to Bangkok flight scheduled for tomorrow. Alas – we headed to the airport, without flight tickets. As of writing, many direct flights for the day are sold out, and each flight went out full today. My wife and I were left with no choice but to shell out for last minute flights, which is as fun for the mind and the wallet as never.

Lessons Learned

This is the first time I’ve been completely burned by a lack of points availability. Sometimes you’re forced to deal with a connection, or fly business when you wanted to fly economy, or vice versa, but SOMETHING almost always works out. I did my research, I had good reason to believe that all would pan out, and yet – it didn’t. I’d say in 100 attempts, I’ve had 99 hits, so this stings, but certainly does not put me off. It does however remind me that I….

  1. Should have reserved refundable tickets as a back up, at the get go.
  2. Set alerts immediately, when I booked my flights to Bangkok, rather than waiting. 
  3. Need to take better account of world events, seasonality and ExpertFlyer load reports. 
  4. Owe my wife a present for causing her a week of stress. We got to the airport today without tickets. Yikes.

Final Thoughts

Points roulette is a lot more fun when you have flexibility. Many of my favorite points moments have come when I’ve had loose plans or intentions, but no specific needs. Living in New York, I used to love saying “what do you think about a last minute DC trip”? If seats opened up, we’d bypass the $750 round trip tickets, use 7,500 points each, score great last minute hotel deals and live it up. If seats didn’t open, we’d stay home. It’s very different when you have places you simply must be – and a lot less fun!

Have you played points roulette? How’d it go?


Gilbert Ott

Gilbert Ott is an ever curious traveler and one of the world's leading travel experts. His adventures take him all over the globe, often spanning over 200,000 miles a year and his travel exploits are regularly...

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  1. Aside on your DC musings: Why would you not take Amtrak NYP-WAS? Just curious as travel time/expense to and from airports seems not worth it.

  2. #4 is obviously the most important lesson learned but great reminder overall..another win is coming eventually to erase this from ur memory

  3. Dang, you win some you lose some. Nevertheless hat’s off to your understanding wife for going along with the roulette game! I can relate and have been burned before taking risky award bets – it’s all about the perspective for this hobby, isn’t it.

  4. Nice to see it happens to the pros, not just us amateurs! Though I’ve made the mistake of paying to reserve fairs for 72 hours with BA and then letting them expire by mistake (double hit).

    Hope you got to relax in the Heathrow Qantas Lounge, that should make up for all the stress.

  5. Always fun to read your articles! Would appreciate if you can do one on how to score last minute hotel deals,

  6. Hopefully everyone here, yourself included, that we’re all playing a game, one in which we take calculated dishes. Like any have, you do but always win and when you don’t, it’s “interesting” to analyze and play Monday morning quarterback, but if you don’t get on the field and take some thought through risks, you can never win. Relax, and go get week next time!

  7. So, it was Trump’s fault?! 😉

    Interesting insight, though, as I look to play my own last-minute roulette game.

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