For the first time I can recall—going back more than two years, at least, and probably longer—I don't have a flight booked to anywhere. I started realizing this as I got closer to flying to Boston last weekend. Combine that with the brand-spanking-new passport I just got, and I feel oddly confined.
So, possessed of a ton of frequent-flyer miles but with no possibility of making the next level of elite status this year, and also facing a dramatic shift in my work-life balance in just over 110 days, I have started plotting my escape.
Where to go, though?
First criterion: Get out of the U.S. A passport without stamps (or creases, scuff marks, bent edges, etc.) just looks sad. Unused. Unloved. Wherever I go in December, then, must get me a passport stamp.
Second: Use frequent-flyer miles. Even though it's August, the number of available seats for miles in mid-December looks pretty grim to a lot of places. Forget most warm spots; forget popular Christmas destinations. At least, not for less than 100,000 miles, and a four-day trip just isn't worth that amount.
Third: Eight hours or less from O'Hare. I'm not relishing the thought of a longer flight for a four-day trip. That rules out Asia, most of South America, and parts of Europe. I can live with that.
So: Candidates. Initially I thought of going someplace warm and sitting on a beach. There are non-stops on American from Chicago to Cancún, Cabo San Lucas, México, and Acapulco. But I'm not really a resort kind of person, and getting anywhere more interesting in Mexico carries risks right now I'm not completely comfortable taking. A connection in Miami opens up the Carribean and Central America; but the number of available seats makes that expensive.
Of course, I'd go to London for almost any reason anyway. It's my second-favorite city in the world, it's only 7 hours away, and in December business-class miles tickets are only 35,000 miles in some cases. But think: London in December? I don't expect to sit along the Thames and sip beer in the six hours of daylight I get before the sun sets just before 4pm.
I think I've settled on Quito, Ecuador. With a connection in Miami it's 7 hours from Chicago (and no overnight flights!). It's reasonably warm. It has living history, being a UNESCO World Heritage site. And very few people speak English, which will force me to practice my Spanish.
More information as events warrant.