Touring Chicago’s architecture by train and boat

I’m on the “L,” Chicago’s elevated train, rumbling past building after building, 20 feet off the ground, when a little voice in my left ear says, “Okay, just before we turn the corner, be on the lookout for the third shell medallion from the end, and tell me what you see.”

I’m on the lookout indeed, and as the train starts to hug the corner around the LeMoyne Building, I watch the lineup of ornaments on its exterior. And then I see it: The shell above one of the exterior pillars is upside-down. “Now you have to wonder,” the voice in my ear continues. “Did they not notice, or was it a joke for the train people? I’m going with a joke.”

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The voice belongs to Lynn Hensel, a docent on this Chicago Architecture Foundation tour, who’s speaking to me through a little earpiece connected to her own microphone and transmitter. Of the 85 tours the foundation leads on foot, by boat and by Segway, this is one of the newest. And I’m taking it because I’m intrigued by the idea of getting a unique perspective on the city’s boisterous architecture from a vantage point offered by what less urban-minded folks might consider just a noisy eyesore. In the so-called City of Big Shoulders, this is like crawling around at knee height.

Hensel weaves her views on building motifs, materials and styles — from the classic Chicago school to neoclassical, modernist and postmodern — together with stories of the L’s development from a series of disparate lines into a unified system in the late 1890s. At the center of that effort was Charles Tyson Yerkes, who apparently strong-armed property owners into giving their permission for the crucial center loop to be built. His tactics involved bribes and the use of “vamps” who seduced and then blackmailed. “By hook or by crook, he got the job done,” Hensel said with a smile.

The tour focus, though, is on the buildings. And what buildings! Chicago’s forward-thinking architecture no doubt stems from the city’s near-destruction in the Great Fire of 1871, and Hensel shows us one stunning structure after another, sometimes closer than you could get any other way short of moving in. When we take a train past the Board of Insurance Building, she tells us that one corner of the building had to be shaved off to give the L room to get by.

Of course she talks about landmarks such as the Willis Tower, Boeing Headquarters, Marina City, the Merchandise Mart and more. But to my mind, the true charm of the tour is in the less well-known spots. Take the Hotel Allegro, originally the Hotel Bismarck, where from a Pink Line train she points out the figures above two windows: the Pied Piper to lure in travelers, and Saint Christopher to protect them. “I’ve walked down this street many, many times,” she says, “and I never saw those windows until I took this train.”

And then there are the outdoor platforms and bridges. As we stand around gawking at one or another of them, listening to Hensel, Chicagoans hurry past us, seemingly oblivious to views they surely take for granted.