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Archive for May, 2011

Road Report: The Windy Apple

Monday, May 2nd, 2011

So I’m in Chicago for the first time in my life. It’s odd. The city feels familiar even though I’ve never been here. I chalk that up to the fact that there’s been a ton of TV and movies that I’ve seen that are based here, but it’s more than that.

As I’ve always said, Pittsburgh is the gateway to the midwest and I’ve always used city comparisons to prove that. Pittsburgh is less like Philly and more like Indy.

That comparison stands up here. Admittedly, Chicago is a much bigger city than all the other midwestern mid-markets I’ve been to, but it feels …well… familiar. I keep thinking that Chicago looks like what would happen if New York and Cleveland had a baby.  It’s big and there’s a Irish bar on every other corner, but it’s also friendly and a little self deprecating.  The streets are wide like they are everywhere that never thought that it would ever be any bigger than it was at any given moment. New York is a city built to be a city. It’s got a grid and it’s laid out perfectly. It’s perfectly measured and no space is left un used. Chicago has that classic midwestern oops about it.

I’m not saying Chicago is a bad town because of that, in fact it makes me like it more. One of the things I like about San Francisco, or Pittsburgh is it feels like a city that kind of constantly outgrew itself. You can see where old parts ended and new parts were added. I know city planners would have a cow if they heard me say that but it’s got a kind of charm about it.

I hear that London and Paris are the ultimate of this – probably to the detriment of traffic, but it adds ultimately to the “homey” feel.

I’ll see if I continue to feel that way when I’ve been here slightly longer than 10 hours.

It's a taxi! But It's on the water? It's a water taxi!