There's no alley equivalent of the Magnificent Mile. The 1,900 miles of backstreets that crisscross Chicago's Grid—more than in any other municipality in the U.S.—are only beautiful for their utility. The city has tried to redefine these corridors of concrete and asphalt in recent years by giving a few of them environmentally friendly makeovers or temporarily transforming them into outdoor venues for art and music festivals. But for the most part they're still a rough and rugged part of our infrastructure—unassuming, unmanicured, and ready to perform a host of important functions while hiding in plain sight.
Though they've existed in some form or another for thousands of years, alleys were considered a waste of valuable space by the planners of older eastern U.S. cities like New York. As urban development principles evolved during the turn of the last century, the concept of big-city alleys—those shadowy areas teeming with disease and danger and vermin—fell out of favor and were supplanted by more spacious front yards in places such as Los Angeles and Portland, Oregon.
It's not as if Chicago's own city planners had "Alley Capital of America" in mind when adding them as a common feature to the urban landscape. They're something of a happy accident, the result of the City in a Garden flowering at the right time in the right place. Chicago was born during a period of the 19th century when cities were laid out in perfectly symmetrical grids because of a legal quirk—the federal government's National Land Ordinance of 1785 neatly divided uncharted territory west of the Ohio River into an interlocking network of 36-square-mile townships. Alleys were a logical way to subdivide a block and keep hidden the ugly working parts of urban life, to ensure the impolite realities of the industrial age (horse shit, the ramshackle housing of the lower classes, et cetera) were out of view of polite Victorian society.
Nearly 200 years later, Chicago alleys lack some of the Dickensian aesthetics but remain the Swiss army knives of urban space. They're where we run our phone cables and electric wires and temporarily store our garbage for collection (which might sound underwhelming until you walk the steaming, trash-heaped sidewalks of Manhattan in the sweltering summer).
Alleys double as your neighborhood's junk drawer—a disheveled bazaar where you can both leave unwanted stuff for others and snag underappreciated goods for yourself. They're conduits of informal social interaction, where kids play in refreshingly unscripted ways, where neighbors converse.
They're also spots of ad hoc privacy that allow us to exercise the messier parts of our humanity in public without utter humiliation. Depending on your blood alcohol level, you can sneak a piss or puke, or make out with a date behind a Dumpster in a shadowy corner while minimizing the chance of becoming a spectacle. Alleys abhor spectacle. They let the streets and avenues and boulevards take all the credit while providing a practical and unpretentious setting where the city can untuck its pants, grab a beer, and let out that fart it's been holding in all day. That's magnificent in a way that would never appear on a souvenir T-shirt. v