One of the craziest things I have ever done

One of the craziest things I have ever done

I was organizing some old photos in Amazon Prime photo vault today and was reminded about one of the craziest things I have ever done. This was in 2013, I was new to the hobby of collecting miles, points and trying to travel the world for little money but in as much comfort as possible. In early November I saw a promotion that American Airlines (AA) was running to steal frequent flyers from other airlines. They offered anyone who was not an AA frequent flyer a challenge – fly 30,000 miles in 3 months and get the highest possible frequent flyer status with them, valid through the end of February 2015. It normally took 100,000 miles over 12 months to achieve that status.

The Executive Platinum status in those days was very lucrative: it pretty much guaranteed free upgrades on almost every domestic flight one took, provided special check-in counters with shorter lines and better service than at first class counters, dedicated phone line that was answered almost immediately, 8 international upgrade certificates and many other great things. I don’t think I had ever flown first or business class before, so I decided to take the challenge and see if I could find out how the other 10% travel.

Well, it turns out that 30,000 miles is A LOT and, in spite of traveling almost non-stop for work for three months, I was going to be only at 10,000 miles or so. Something needed to be done and I started looking for a good mileage run somewhere far and cheap. Europe was not far enough, even Australia and New Zealand were not enough. Fortunately for me, I found an inexpensive fare to Singapore on Cathay Pacific that is one of the best airlines out there. And Singapore is one of the farthest places on this planet from the US. Here is what my flight route looked like.

9, 381 miles one way

The route itself or even taking part in the challenge itself were not the crazy part. I could only do it on the weekend and could not take almost any time off work because of all other trips that year and an important meeting in DC I could not skip.

With that in mind, I booked the following trip: leave Chicago for Hong Kong at 2pm on Friday, arrive in Hong Kong at 8pm on Saturday, spend one night at an airport hotel, leave for Singapore at 8am on Sunday, get there at noon, stay for 13 hours and leave for Hong Kong at 1 am on Monday. With the time difference and a short connection in Hong Kong on the way back, I was going to arrive back in Chicago just after 12pm on Monday. This gave me 1 hour and 45 minutes to clear immigration, transfer to another terminal and catch my 2pm flight to DC, where I had to attend a meeting on Tuesday.

Did I mention crazy?

It was actually not as bad as it sounds, every flight was on time, I got to eat some amazing food both in Hong Kong and Singapore, realized that I definitely want to come back for a longer visit and I did complete the challenge. Shortly before Christmas that year I got the Executive Platinum status and actually enjoyed the process of flying in the US for over a year! I know, it is hard to believe 🙂

Oh, and I am going back to Singapore in September. I will be there 3 days this time and will share my thoughts on that amazing city at

What was the craziest travel-related thing you have ever done? Tell me in the comments.

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