There were supposed to be more of them. It was in the Plan. (You know which Plan.)
In the Plan, diagonal streets spanned the city like the Hancock Center's Xs, creating crosstown routes and turning perfectly perpendicular intersections into junctions of six or even eight corners: 51st and King, LaSalle and Ohio, Western and Fullerton.
But Chicagoans love Daniel Burnham's Plan mostly in theory, and so today the city has fewer Grid-defying streets than in 1909, when Burnham and his coauthor, Edward H. Bennett, made their recommendations. (There's probably some Mark Twain quote about the Bible that would be applicable here, along the lines of "often cited, rarely read." That's how Chicagoans love the Plan.)
Our one experiment with adding a diagonal—extending Ogden from the west side through Lincoln Park—was reversed when the Lincoln Parkers thought it ugly and unwarranted (they never wanted to go to the west side anyway). And in the mid-20th century, city planners decided to give already existing diagonals the ax to make room for other things. They cut out a mile or so of Blue Island Avenue to build UIC. They eliminated an angled section of Cottage Grove north of 35th to build Lake Meadows. They bulldozed a block of Fifth Avenue on the west side for a highway, and another block for a school parking lot.
But maybe it's not so bad. Maybe we just need to do a better job of appreciating the diagonals we have. The paeans to Clark and Milwaukee and Archer are numerous. What about Talcott or Forest Preserve or Manor or McDowell or Vincennes or Exchange or Van Vissingen? For that matter, what about all the streets only masquerading as upstanding members of the Grid? On the west side, road after road gets corrupted at North Avenue, each one dancing to the east for a brief stretch: Kedzie and Pulaski and Cicero and Central—all diagonals for a moment. Lake and Devon and Grand, too, loosen up once they get far enough away from the shoreline. Even Michigan Avenue runs diagonally, if only for a block or two, just north of Old Fashioned Donuts in Roseland.
What's special about diagonals, after all, is that they follow their own rules. A grid promises predictability, the geometric comfort of a forever-repeating pattern. Some homesick Chicagoan in Brooklyn can do the math to determine that he lives 440 blocks south of Madison and 4,998 blocks east of State. Surely anyone who's lived in Chicago long enough has come across an unrecognizable block of his own street miles and miles from his home and expected, at least for a moment, to see his doppelganger living a twisted parallel life.
The best diagonals, in contrast, are short. They can be yours in ways that a lengthy linear street just can't: Western or Chicago are vast enough that they begin to seem more like lines of latitude than streets belonging to particular neighborhoods. Look in either direction down a gridded street and you'll see the horizon; a good diagonal will show you a brick two-flat with a gray vase in the front window and a concrete stoop. In that spirit, my nominee for the very best diagonal in the city measures just a few hundred feet: the 2400 block of North Albany, which is lined with trees and graystones and makes for a handy shortcut from Kedzie Boulevard to a corner store near my old apartment. v