When it comes to tallying up the estimated total cost of my trip, I keep adding that into the “do later or never” pile. I wouldn’t refer to myself as “money bags”, and even if I did, I would be focusing on saving money where I can (to hold onto that nickname)! For now, let me tell you about a score that I found when I booked my flight from New York/Newark to Singapore, non-stop, one-way on United Airlines.

Since I am a frequent flyer with United, and once upon a time I accrued a lot of miles on a credit card (responsibly, of course…) I have something like 100,000 miles sitting around and gathering dust. I guess I haven’t used mileage as often as I could have in the past because, like George Clooney in “Up in the Air”, it wasn’t about redeeming mileage, it was just about amassing as much as you can.

Six weeks it became clear to me that the window for my “epic sabbatical around the world” was approaching, which wound up consisting of just five countries for now in Southeast Asia, and I realized it was time to either put up or shut up with my planning and actually purchase the air ticket(s). I went to my old standby, Kayak.com, which I use pretty much exclusively for looking up or booking airfare. I think that all travelers are a little cautious about the airline they choose, preferring to stick with a well-known brand at a higher price, than an unknown airline or one with a poor reputation (see: Malaysia Airlines…). The best price I found was in the neighborhood of $700, flying from New York/Newark to Singapore, with one stop, maybe in Frankfurt, Doha, or Tokyo–can you tell I’ve done this route a couple of times? Just to reiterate, this is for a one way ticket. I’m not sure exactly when I’ll be coming home, or even from which airport, so one way suits me for now.

Out of curiosity, I logged into United Airlines’ web site and pulled up “rewards travel”, leaving the whole month of February open for my travel. Why February, why not January or March? Some of the reasons are logical and some are complete nonsense, but for my memory and for your delight, here is my reasoning:

1. I had the house to myself for the month of January (PARTY)! Actually, my idea of partying is putting the heat up to a comfortable temperature…
2. I wanted to give myself enough prep time for the trip. Considering the time it took me to set up a great bank account (no foreign exchange fees!) and receive an assortment of time-specific vaccinations, this worked out pretty well. And if I waited for March, I’d be cutting my trip shorter and shorter since I need to be back at the beginning of August no matter what.
3. Most importantly… I need to give myself a window to see 50 Shades before I declare an official timeout from America.

A few clicks and scrolls later, and I was looking at the pricing for my awards travel. A grand total of 40,000 points PLUS a whopping $18 USD in fees.

Now, I don’t know what the airlines would tell you, but for me I believe this to be accurate. You can consider 10,000 miles to be the equivalent of paying $100 USD out of pocket. Whether you’ve amassed those miles through flying, credit cards, or some kind of promotion. The taxes and fees can be as little as $2.00 but I’ve seen them as high as $150, and often when buying a round trip ticket you’ll see that the fees in one direction are very cheap whilst the fees in the other direction are very high, giving you an average of something like $60 to $75 in fees per flight segment.

In other words, for the same flight route I should have expected to pay a minimum of 70,000 miles plus a higher dollar amount in fees. While there are lots of secrets to shopping for tickets, including the day of the week that you purchase, a series of settings like cookies and geographic tracking in your browser(s), and lots of ways to beat the system (hint: the airlines have very sophisticated revenue models and like Vegas, the house always wins), and more. In this case, being flexible with my departure date, using mileage to my advantage, and just old-fashioned luck really worked in my favor.

My travel tips to you: enroll in frequent flyer programs whenever you can and whenever possible do your shopping in such a way that it benefits you overall and your mileage in particular, shop around on a couple of websites, be flexible, and though I got lucky six weeks out you may want to try looking further in advance. Good luck and bon voyage!