Most American cities are organized on an unrelenting grid, an artifact of early European settlers’ simple and unimaginative approach to land surveying and real estate speculation. While most of Chicago’s well-noted architecture has been built on this grid, our major diagonal streets create numerous “flat iron” sites across many neighborhoods.

The North Side abounds in these anomalies, including Clark Street, Broadway and Lincoln, Milwaukee, Elston and Clybourn avenues. There are fewer on the South and West sides, most prominently Ogden, Blue Island and Archer avenues. And while not all of these diagonal streets reach the Loop, it’s unusual for them not to point in that direction (Ogden being the most obvious example that originally terminated at the old Chicago Academy of Sciences building in Lincoln Park).

The term flat iron building can be applied to any triangular-shaped structure with an acute angle, so named for a resemblance to the old-fashioned cast-iron home appliance for pressing clothes. The most famous example is Chicago’s by provenance, the Daniel Burnham-designed building in New York at the corner of Fifth Avenue, Broadway and 23rd Street. Completed in 1902, that 22-story-high structure quickly became iconic through the 1903 photograph by Alfred Stieglitz and a 1904 photograph by Edward Steichen. New York’s Broadway creates similar sites along its path, but only the old New York Times building (1904, Cyrus L. W. Eidlitz) between 42nd and 43rd streets has much architectural presence — it gave Times Square its name and provides the base for the annual New Year’s Eve ball drop.

Chicago has a lot more versions, although we don’t really celebrate them enough. The straightforward terra........

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