"Wishing you a wonderful stay in Boston, or wherever you final destination might be..."

Hopefully by the time I post this I’ll be happily settled for the night in Boston, enjoying my visit and looking forward to a much-needed brunch in Boston’s South End tomorrow.

I’m finally on my last flight of the “day,” going from Chicago to Boston. It’s thankfully my shortest flight so far and is only about half-full, giving me the exit row to myself. All in all, I’m pleasantly surprised at how this experience is going. I’m feeling decently rested, having slept at least a few hours of each flight to date, and the weather and planes have decided to behave enough to let me make all the connections.

There’s a strange sense of camaraderie amongst the other frequent flyers who are trying to cram in their last miles of the year this weekend. Without fail, each Admiral's Club I’ve stopped in at this trip has had at least one person at the desk saying something to the effect of, “I think I need about 3,000 more miles, how many will the round-trip to Miami get me?” The reason for this is that not only is it near the end of the qualifying year for American Airline’s Elite Status program, but until the 15th of this month, they are doubling the qualifying miles flown. To be sure, it’s a strange thing to care about, but we all have our little obsessions. Moreover, when you’re already flying more than once a month, the little things like an upgrade now and then make it much more enjoyable.

For anyone who might consider doing something similar to this in the future, here’s what I’d tell you. Watch the weather, and try to make as few connections as possible to limit the chance you’ll get delayed. However, when I do make connections, I like to have more than an hour just in case. Also, when traveling in and out of O’Hare, be prepared that: 1) Tight connections/delays are common which often leads to stress, panic, and outright theatrics amongst your fellow travelers as you sit on the runway on your already late flight for the even later flight ahead of you to clear the gate, and 2) The wind currents and turbulence generally make holding patterns and landings about as smooth as bottom-shelf whiskey. That said, the Admiral’s club by Terminal H is very comfortable, and isn’t a bad place to wait out your delay.

Before I head off into the 30 degree Boston night for a real night’s sleep, I’d like to leave you all with one friendly request. From someone who has just gotten onto and off of 9 flights in the past three weeks, and has 6 more to go in the next two, the next time you get on a plane please do your fellow passengers a favor and organize yourself. What will you want out for the flight? Do you have two carry-ons? Which is bigger? In short, one simple rule: Roller-Bin, Bag-Floor, You-Seat. This should take about 10 seconds.

Thanks for reading, and until I’m back in the air late tomorrow, good night and safe travels.