As you walk down a typical street in Manhattan the first thing you notice is just how straight it is. Roads in Manhattan have actual vanishing points, like railroad tracks. You walk slowly towards this point that you will never reach, and the cross streets come up one at a time, at perfectly spaced intervals and at perfectly right angles. First you look left, and then you look right, and you're taken aback at how perfectly straight those roads are as well, and how they also seem to go on forever in the distance.

It feels like Manhattan is made up entirely of infinite streets. It's so big that you feel like you're missing out on most of it, like each road you pass on your way to your destination is a lost opportunity, a story you'll never get to hear. You feel like there are countless Woody Allen movies and Seinfeld episodes going on at the same time but you'll never know anything about them because you didn't choose to walk down those roads. The sense of loss can be very powerful.

Paradoxically, Manhattan can also feel claustrophobic. You feel like you're jostling for space with every other inhabitant of the City. The buildings are mind-numbingly tall, and some of them are even beautiful, but you rarely see them "in the distance", unlike the vanishing point that you'll never reach, and you often have to crane your neck to get a good view.

On the other hand...

New York City may be home to countless stories but Chicago is home to just one. It's a good one, though, and it takes place at night, in the rain, with slick, shiny roads reflecting garish and lurid neon signs above an endless parade of shady establishments. It's a story populated by men who wear fedoras and carry guns and conduct questionable business in secret alleyways beneath the L train, and with dangerous, dagger-wielding women who wear blood-red lipstick and blood-red evening gowns and blood-red shoes. Women who'll kill you with a dismissive, disdainful look before they bury a knife in your back.

Chicago does not feel as claustrophobic as Manhattan. The streets are wider and the skyscrapers are laid bare in front of you like a metropolis-sized picnic made of concrete and steel, inviting you - nay, daring you! - to gawk. The buildings look like they belong in a different era, because they do, and it's almost as if your eyes begin to involuntarily develop the ability to see the world in sepia.

Drinking in Chicago feels naughtier than drinking in New York City, given the former's history. It's stupid - I mean, New York had Prohibition and gangsters too, but somehow they just don't stick out like they do in Chicago. New York just doesn't seem as gritty, which is weird because New York is physically so much dirtier than Chicago and New Yorkers are so much ruder. And yet, somehow, you leave New York with the sense that anything is possible, while you leave Chicago with the sense that the Man will always get you in the end.

[As you might have guessed, Evelyn and I recently visited New York City and Chicago. Photos are available in my gallery]