Despite my love of big cities, I somehow didn’t make it to Chicago until I was 35 and then never made it back. So when Solar had a week long conference there—giving me a free place to stay right on the river—I decided to join. Why not? And when he suggested we extend the stay through the weekend since he has friends there we could stay with, again, why not? And so my United rewards ticket carried me off. With the exceptions of the view of Trump tower from my hotel and the weird sewage smells that hit my nostrils from time to time as I roamed the city, the trip was fantastic. Every day brought fun experiences, and here are the three best days.
My first international flight, which was also my first flight ever, cost $899 one way. It was scheduled to go from Buffalo to New York City to Manama to Melbourne. A snowstorm in Buffalo derailed that plan, so I ended up on a flight from Buffalo to Washington, DC to London to Singapore to Melbourne. This was back in the day when airlines took care of their passengers when things like this happened, no travel insurance needed, so my unexpected 14 hour layover in London came complete with a free stay in the Radisson Edwardian for the day, lunch, dinner, and transportation to and from the airport. Then I ended up in bulkhead seat (back in the day when you didn’t have to pay extra for those) on a double decker Quantas plane all the way from London to Melbourne. Not a bad outcome for a highly price conscious 19 year old.
I never played the airline mileage game until a few years ago, which was really a waste considering how much travel I did and how many miles I could have earned. I always looked for the cheapest flight possible. The best deal I scored was round trip on Air Transat from Toronto to Frankfurt, Germany for $425, all fees included, back in 2001 just before the TSA ruined airline travel for all of us. Sometimes I got lucky and landed deals on luxury Asian airlines, like Cathay Pacific from Melbourne to Bombay, with a free three day layover in Hong Kong. If you’ve never flown an Asian airline, you have to try it. Our first class is their economy. And I got an amazing package holiday deal to Iceland when Iceland Air opened direct flights from Denver to Reykjavik. Continue reading →