Chi-town with Kay

This time next week, minus the time zone difference, I'll be in the air, an hour away from Chicago. Who flies on New Year's Eve, you ponder? Jonathan and I do. And if we happen to get stuck in the airplane, I hope they have a full stock of those tiny airplane-sized bottles of booze, because one way or another I am putting on my pretty dress and getting drunk in another state.

Operation Chicago with Kay is going to take some preparation. First of all, we're landing at 11pm, and I'm going to have to do everything in my power to fly with carry-on luggage only. Second: train or shuttle or cab or private car? It's NYE and I don't want to get stuck in traffic, and trains generally don't. But I had this image of jumping off the empty plane (a week before the flight, tickets are $94 one way) the second the doors open, wearing my gold bubble-hemmed party dress with fishnets and tall heels, getting into a black car, and arriving at my destination with a black duffle in tow like a true jetsetter (on a budget, that is). So maybe it'll be a gold party dress on the train. It's NYE, anything goes, right?

Problem three. I don't know where my luggage is. Problem four, I KNOW I'm going to forget to charge my iPod, so I'll probably have to play sudoku and bother Jonathan the entire flight there and back (this one is less a problem and more a prediction, so, uh, don't forget to pack those nerves of steel, JW!) solved! I charged and updated my ipod - how proactive of me.

Five. I never know what to pack for weather different than my own.

Six. I often forget my toothbrush, hairbrush, or any styling products that aren't already on my head.

Seven. Phone charger. I never take it with me. I hope my phone can handle 3 days without a charge, but I'll probably be transit-mapping and yelping my way around town so that's doubtful.

Eight. In bouts of compulsion, I always end up buying something when I go away, even for a few days. So I have to somehow allow room in my luggage, which is going to be overhead only and so very tight for space to begin with. It'll probably be shoes. Hopefully boots. Mmmm boots.

These are just eight of the ways I present a challenge to myself on a daily basis. Will do some kind of an update in a week because it'll probably be some kind of a hilarious blunder.