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Ask Chicagoist: What's Up With the Diagonals?

By Thales Exoo in Miscellaneous on Feb 22, 2006 6:38PM

I know that Daniel Burnham's Plan for Chicago was all about the grid system (or that's what I've been told at least). So what's the deal with Milwaukee, Elston and Lincoln Aves? Were diagonal streets part of that plan or did they evolve later? And why? They always mess with my sense of direction so I'd like a reason to stop hating them.


Chicagoist has a reputation for getting lost walking around the block, so we completely sympathize with any directionally challenged related concerns. Since living in Chicago we've been a little more sure of ourselves, however; the grid layout of the streets and easy numbering system has us almost fooled into thinking we know where we're going.

In 1909, Daniel Burnham published the "Plan of Chicago" -- a proposal for Chicago's development that would become a textbook example of American urban planning. It outlined ideas for green spaces and parks, lakefront development, highways, railroad use and location, cultural centers, and yes, the layout of our streets. The Plan recommended a "systematic arrangement of the streets and avenues within the city, in order to facilitate the movement to and from the business district." As always, it's all about buying stuff. This directive translated into the development of the grid system. With few exceptions, Chicago's streets are arranged so there are eight blocks to every mile, with each block incrementing the addresses by 100. The north/south dividing street is Madison Avenue, and the east/west divider is State Street. Easy enough. But what about those pesky diagonals?

Part of Burnham's big vision for Chicago was a grand civic center which would serve as the center of the city, and be easily accessible via diagonal streets radiating outward. This part of his plan was never implemented. In fact, the only new diagonal added to Chicago as a result of Burnham's Plan was an extension of Ogden Avenue. If his scheme had been fully realized, there actually would be even more diagonal streets in Chicago, the theory being that the quickest path between any two points is a straight line.

So that doesn't really answer your question, does it? If we can't blame Burnham, who can we blame? Well, it turns out that most of Chicago's diagonal streets were originally Native American trails. No, really. Milwaukee Avenue (originally West Plank Road), for example, was once a buffalo route that led to the Chicago River. Eventually settlers moved in, kicked the Native Americans out, and started building taverns along the trail. Once there were taverns, homes and businesses cropped up and the street thrived. Sound familiar? These diagonal paths in the city (Lincoln was Little Fort Road, Elston was Lower Road, Ogden was Southwestern Plank Road) became plank toll roads, and then finally regular streets that serve as some of the major arteries of Chicago.

Feel like you're walking in circles? Need some advice? Email ask(at)