Crossing Chicago

A catalog of urban transport in the Windy City

“Pigeons.” 2019.

A transit of Venus or Mercury occurs when one of these planets passes between Earth and the sun and is therefore visible to observers on Earth as a dark spot moving across the face of the sun. Early astronomers used such transits to estimate how far they were from the nearest star. In this way, the movements of relatively small bodies, discrete moving parts of the dynamic whole, might be used to imagine the scale of the solar system or, indeed, of the universe.

The city of Chicago is roughly 25 miles long and 15 wide. The Chicago Transit Authority, the nation’s second-largest public transportation system, operates 1,864 buses on 129 routes and 1,492 railcars on 224 miles of track, including 35 miles of elevated—El—structures. The regional Metra network operates another 840 railcars on 1,155 miles of track, having absorbed remnants of storied railroads such as the Union Pacific and Illinois Central. A record 919,704 flights arrived at or departed from O’Hare Airport in 2019, when it was the world’s busiest; another 232,084 passed through Midway. Driving a car, cozy in your own sovereign mobile microstate, you can pass through the city shielded and buffered from other lives and their consequences. On public transportation, it’s a different story. 



Late afternoon traffic was thick on Stony Island Avenue, a major north–south thoroughfare that traverses the South Side from Hyde Park to the Calumet River. I was on a bus on my way home from school—sitting near the back, as usual, looking out the window, deep in the fugue that riding the bus tended to bring on. I don’t remember the season, though winter’s the default in my childhood memories of Chicago in the 1970s.

My southbound bus was temporarily stopped. In a northbound lane below my window, a bird stood on the pavement. A sparrow: plump, chesty, gray-brown. The bird looked up and to its left, and I thought to see something fierce, pissed off, all at once defiant and resigned and futile in the set of its head and the way it just began to square itself, set itself—and then a northbound bus, taking advantage of a gap in traffic to speed up, filled my vision for a long, streaming, green-and-dirty-chrome moment. When the bus had passed, the bird was gone, with no trace of it ever having been there. No lump, no stain, no single feather floating to the pavement. Northbound traffic picked up and more cars passed. Then southbound traffic started rolling again, and my bus lurched into motion and continued south.

Bird, bus, no bird. That’s the whole memory—vivid, self-contained, seemingly ineradicable after half a century and counting. The bird looks up, sees something huge and fast coming, and is gone. I can’t tell if there was just time for it to resolve to die well, if birds even do that, or to dive between the bus’s fat tires and then somehow fly off without smacking into its hot stinking metal underside or a passing car. I could—I still can—imagine the bird as impossibly brave, or brimming with rage, or serenely fatalistic, or wholly caught up in the dire mechanics of the moment. Its inner life, opaque to me, becomes a blank screen onto which I can project my own.



Toronzo Cannon drove a CTA bus for 26 years and a day before retiring to become a full-time bluesman. His main route was the 157 Streeterville, which, he told me, “goes from the poorest West Side, Pulaski and Cermak, to Water Tower,” on the Near North Side’s Gold Coast, the city’s showcase shopping and tourism district. “There were 22 turns on the 157 route,” he said, and each of those turns would cause the bunch of keys dangling from the ignition to swing. They would jangle in a rhythm that seeped into the songs he wrote in his head. He would also overhear things passengers said—such as “I need a boyfriend, Christmas is coming”—and try to work those lines into songs. He kept scrap paper on hand so that he could scribble something at a red light, but sometimes he’d have to pull over to get an idea down properly. “Everybody on the bus would get concerned,” he said. “‘Why is the driver getting off? Is something wrong?’” He’d be out there on the sidewalk trying to extract music from the 157 route, humming and muttering into his phone to capture the song before it flew out of his head or was wiped out by the repetitive routines of the work day.

A left-handed guitar player with a warm humbucker sound, Cannon mostly works without a rhythm guitarist, steadily comping and playing tasty fills behind his own singing and trying not to go overboard with his solos. There’s something solid, steady about his kind of blues. It sticks to your ribs, reliably transports you from here to there without any showing off. Cannon may lack the divine spark that sets apart a towering virtuoso such as Buddy Guy or Otis Rush, but the genre can’t thrive without competent high-end journeymen, and he’s as competent as they come. He also writes a lot of songs, and Chicago blues needs fresh songs. Sometimes he stuffs too many syllables into the lines of the songs he writes, though to my ear that’s a fault that comes of a virtue: he cares about the words. He can write a resonant blues line, especially about the feeling of having been wronged. For instance, “I been better to you than I been to myself.” If I heard somebody say that somewhere behind me while I was driving a bus, I’d pull over to write it down. 



Wherever I’m At, a collection of poems about Chicago published in 2022, contains several public transportation poems—which seems only fitting to me, since a collection of poetry is a sort of conveyance to transport the public. In one of them, Tara Betts meditates on the procedures of transport as she listens to native Chicago soul singers Donny Hathaway and Minnie Riperton on headphones while riding a 72 bus eastbound on North Avenue: 

When you count the breaths to your stop, wondering 

why you love the route & find yourself silently pleading

to stay. You lean deep into your seat, press repeat since 

nostalgia becomes a contradiction of armor & comfort. 

In another, Albert DeGenova recalls seeing Gina DiDomenico at a bus stop on 55th Street every morning, which led to asking her out, then months of necking in the rearmost seats of what they (and also the people I grew up with) called “the green limousine,” then prom, marriage, divorce. The route has a generational feel of eternal return: Years earlier, my mother waited on the same corner, met my father on the Archer bus, he would get on at Lockwood Ave, they’d ride downtown together—Mom was a ticket girl at the Chicago Theatre, Dad worked at the Palmer House Hotel. They divorced too. Riding the bus, an exercise in simultaneous intimacy and solitude, requires armor but also dispenses comfort—the kind of contradiction that produces poetry like a grain of sand in an oyster produces a pearl.



On both the bus and the El, you share a metal tube with strangers, seeing and unseeing each other according to custom and usage and the calculus of risk management, and on both you look out the windows at the city. But the greater height and speed of the El take you into and out of other people’s lives in distinctive Hopper-Hitchcock flashes, seen through the windows of their second-story apartments. Those lives pass in clickety-clack film projector frames-per-second as you pass in a clackety-clack railroad din: a young woman looking up from her phone just in time to almost exchange gazes with you; an old guy with flyaway bedhead absorbed in reading the newspaper at a kitchen table, spoon in hand and a bowl in front of him.

“Bungalow Family.” 2018.

Stuart Dybek’s short story “Pet Milk” follows the progress of a Chicago couple already pulling apart as they pursue their own trajectories out of the old neighborhood and into the middle class. “Pet Milk” is about lives intersecting and separating—about missing someone you’re with, being there and not there at once. On a valedictory sunset ride on a northbound El train, the couple slip into the empty conductor’s compartment, the door clicking shut behind them. “We were kissing, trying to catch the rhythm of the ride with our bodies. The sun bronzed the windows on our side of the train. I lifted her skirt over her knees, hiked it higher so the sun shone off her thighs, and bunched it around her waist. She wouldn’t stop kissing. She was moving her hips to pin us to each jolt of the train.” But the narrator’s already drifting away—forward into a future in which the two have already gone their separate ways and also backward into memories of the familiar landscape through which the train moves: “past scorched brick walls, gray windows, back porches outlined in sun, roofs, and treetops—the landscape of the El I’d memorized from subway windows over a lifetime of rides: the podiatrist’s foot sign past Fullerton; the bright pennants of Wrigley Field, at Addison; ancient hotels with TRANSIENTS WELCOME signs on their flaking back walls….”

The very last thing he sees from the train window is “a high school kid in shirt sleeves, maybe sixteen, with books tucked under one arm and a cigarette in his mouth,” who grins and starts to wave as he spots the couple in the window as they flash past him. “It was as if I were standing on that platform, with my schoolbooks and a smoke, on one of those endlessly accumulated afternoons after school when I stood almost outside of time simply waiting for a train, and I thought how much I’d have loved seeing someone like us streaming by.”



Three young men in a movie wait for a train on an El platform. It’s the ’70s; it’s cold. Richie and George wear drab winter gear and carry instrument cases, a guitar and a horn respectively. Kevin, a singer, wears a broad-brimmed magenta hat with a white band around the base of the crown, a full-length black leather coat, voluminous mauve pants and platform shoes. Kevin, who is Black, is exhorting the others, who are white, to loosen up on stage. “You gotta start movin’ a little. You gotta stand out there, play that axe”—he mimes playing a guitar with shoulder-dipping, hip-swaying funkiness while stepping in place, à la Earth Wind and Fire. “Gotta be bad. Yeah, that’s what you gotta do, Jack. That’s what’s wrong with you.” Richie and George exchange half smiles, amused rather than offended. This seems to be a familiar riff, and they’re all friends, bandmates. Richie says to Kevin, who grew up with him in the South Side neighborhood of South Chicago, “You’re the only person I know that does a floor show for everyone on the El platform.” Kevin spreads his arms and declaims with mock profundity, “The whole world is a stage.” Kevin, played by Edward Stoney Robinson, a promising actor and musician who died of a blood disorder less than a year after the film’s release, pauses for a moment and then adds, “It’s obvious.”

When they’re not rehearsing or performing, the characters in Stony Island move around the city, doing much of their thinking and talking on platforms or on trains or riding around in cars. Tracking them in motion, the movie also suggests greater flows of people into and through the city. Kevin digs Richie’s stories of his ancestors uprooted from the shtetl by pogroms, digs country music, digs everything because he’s a beautiful cat. Percy Price, the old head who shepherds Richie, Kevin and the rest of the movie’s eponymous interracial R&B group through heartbreak and conflict to funky success, offers another model of open-minded cosmopolitanism. A Jewish cantor sings at Percy’s funeral, as does Ronnie Barron, doing a Dr. John turn as Ronnie Roosevelt, a luminary from New Orleans who comes to Chicago for the funeral. Roosevelt travels by train, retracing Percy’s original journey as part of the Great Migration. Stony Island wants to say that these swirling flows of folk migration from places as varied as eastern Europe and the Mississippi Delta, movements that have historically given rise to social tension and violence in Chicago, have also produced the kind of satisfying tension and release that make for sweet soul music.

Released in 1978, Stony Island captures for posterity an order of R&B that flourished in the late ’70s and early ’80s: a little jazzy and not very disco at all, with soft-edged funk and rock touches and hints of blues and gospel influence, all under a smooth veneer that often brings it closer to Anita Baker or Earl Klugh than to the Isleys or O’Jays. Noted local session men such as Phil Upchurch and Tennyson Stephens play band members, and the veteran saxophonist Gene Barge, who in his long career worked with everyone from Muddy Waters to Natalie Cole to Public Enemy, plays Percy Price. Several members of the young cast—Dennis Franz, Rae Dawn Chong, Susanna Hoffs—went on to bigger things, as did the director, Andrew Davis, who parlayed his soulful indie calling card into opportunities to crank out bigger-budget Hollywood sausage links such as Above the Law, The Fugitive and Collateral Damage. Chicago-based talent that enters the mainstream often ends up flowing to one coast or the other.



The mother of all the many train rides in Chicago’s literature takes place in the first chapter of Theodore Dreiser’s novel Sister Carrie, published in 1900. It’s not the first such ride—the scene of arrival by train was common enough to become a recognizable motif in early Chicago writing—but Sister Carrie’s has come to be regarded as the canonical one. In that chapter, a young woman named Carrie Meeber takes the train from Columbia City, Wisconsin, to Chicago, which seems to expand outward across the Midwest to meet her. “Across wide stretches of flat, open prairie they could see lines of telegraph poles stalking across the fields toward the great city. Far away were indications of suburban towns, some big smokestacks towering high in the air. Frequently there were two-story frame houses standing out in the open fields, without fence or trees, lone outposts of the approaching army of homes.”

“Bungalow Family.” 2018.

During this ride, she encounters a salesman, Charles Drouet, who deploys squeaky shoes, an overstuffed wallet and other impressive talismans of big-city belonging to close the range on her so that he can extract the address of her sister’s place, where she will be staying. “Now she felt that she had yielded something—he, that he had gained a victory. Already they felt that they were somehow associated.” They are “nearing Chicago” in every sense of the phrase, as the “half-equipped” Carrie has already embarked on the process of fully equipping herself by becoming a city person, an actress adept at reflecting others’ desires back at them, a pro. But Drouet’s mistaken in assuming that he has the upper hand. Carrie will soon eclipse him, upgrade to a fancier and even more boring boyfriend, move to New York with the new boyfriend, dump him as well, make it as a chorine and then a breakout star on the Broadway stage and eventually realize that she has the urban skills to make it on her own without a man in tow. It’s all foreshadowed in that Chicago-bound train ride.



About a century later, Liz Phair arrives in Chicago by plane in the song “Stratford-on-Guy”: 

I was flying into Chicago at night

Watching the lake turn the sky into blue-green smoke

The sun was setting to the left of the plane

And the cabin was filled with an unearthly glow

In 27-D, I was behind the wing

Watching landscape roll out like credits on a screen

“Karolinka Club.” 2021.

The song appeared on Phair’s debut album, Exile in Guyville, which was received as a riposte to the Rolling Stones’ Exile on Main St. and a stinging rebuke to the sexual and cultural politics of the neobohemian Wicker Park scene from which she emerged. Though entry by air had replaced rail as the mode of transportation that allows a special perspective on the city, Exile in Guyville was the opening move of a career with Carrie-like features: Liz Phair came to Chicago from its northern hinterland (Winnetka, a suburb) and eventually moved to an even bigger entertainment capital on the coast (Los Angeles), where she became more conventionally successful (making highly produced pop music and scoring TV shows).

This glamorous career arc caused bitter gnashing of teeth among the authenticity police she left behind in Wicker Park. But when Exile in Guyville came out in all its lo-fi glory in 1993, Liz Phair was indisputably what was happening. No matter how cool the biggest Wicker Park rock snob understood himself to be, he knew that he could not possibly be too cool for that album—or even, in his secret heart of hearts, cool enough. Part of what made Phair so cool was that she not only exemplified but also mocked everything rock snobs cared about. The parodic edge showed up not just in the lyrics but in the form of her performance, especially the wobbly pitch and tone that came of intentionally dropping her voice too low for her range and singing without vibrato. It qualified as conventionally “bad singing” that voice coaches would eventually correct, but it was also a shrewd bust on the male voice of the music scene, the Planet of the Guys culture that dominated Wicker Park and the larger world of rock critics and musicians.

Epic and mock-epic at the same time, kidding and also not kidding at all, “Stratford-on-Guy” paints the city’s panoramic portrait from the air with poetic ambition:

The earth looked like it was lit from within

Like a poorly assembled electrical ball

As we moved out of the farmlands into the grid

The plan of a city was all that you saw

And all of these people sitting totally still

As the ground raced beneath them, thirty-thousand feet down



Above, in the background, a plane about to land descends toward the white wall surrounding Midway Airport. Below, in the foreground, a lean woman in a gray T-shirt, her red hair whipping over her eyes in the wind, takes a break from cutting the grass to strike a proud Whitmanian pose, one gloved hand on cocked hip and other, ungloved, laid on the lawn mower’s handle.

A guy in shorts and a T-shirt sits and smokes on what looks to be a box-like hunk of rock set by the door of the Karolinka Club, formerly the Baby Doll Polka Club, across the street from the airport wall. He’s in shadow, while a plane overhead takes off into bright sunlight.

A shirtless guy with a beer gut and a big, fading tattoo on his fleshy upper arm sits on the bench in a bus shelter. Rendered ghostly by tricks of light in the plexiglass of the shelter, he’s turned to look at the camera. He holds his glasses in his hands, which are in his lap. Cars pass in the street in front of him, and a plane is coming in for a landing, just about to pass over the wall. 

For most of the past decade, Paul D’Amato has been taking pictures in neighborhoods around Midway Airport: Chicago Lawn, West Lawn, Brighton Park, Garfield Ridge. Midway is Chicago’s mom-and-pop airport, snugged into the fabric of the city at its western edge. The bungalows crowd close to the airport’s high white wall, and the planes come and go, engines roaring, above the everyday routines of neighborhood life. “Just about every ethnic group in the city lives here against a backdrop of strip malls, fast food, motels, light industry, shipping and transportation,” D’Amato has written. “Everyone is midway between poverty and middle class, all striving to be somewhere else, although very few have flown on the jets that make their dishes rattle every seven minutes.”

Even when there’s no plane in sight, his Midway pictures convey a sense of scale, of larger forces—physics, economics, the power grid, nature, human nature—operating above and around the mundane. In his descriptions of individual photographs, D’Amato often remarks on the serendipity of stumbling upon a scene, a moment of convergence. On his way from here to there he saw this woman cutting the grass, or this guy pumping gas, or this tree in front of a bungalow; he realized that the wind was right, so that planes would be coming in from an angle that put them in the picture; he pulled over, jumped out, started shooting. The rich inner life of the images also derives from the tension between capturing such a moment—freezing it, elevating his characters into icons—and the pervasive sense of passage in them, of people and objects and processes in motion. They are already leaving this moment behind to disappear as if it had never happened. D’Amato has written, “Midway is somewhere between becoming and being, between entropy and stasis, between learning and knowing, between alienation and belonging, between isolation and community, between immigration and assimilation, between urban and suburban, between poetry and blight. Midway is a metaphor and it’s a state of mind. It’s also an airport.”

• • •

Two kinds of transport, aesthetic and physical, meet in Paul D’Amato’s pictures, Toronzo Cannon’s blues, the work of the bus-riding poets, the intersecting trajectories of characters on trains and platforms, the four-second Iliad of my sparrow on Stony Island Avenue. In this way, the movements of relatively small bodies, mere dots in transit across the face of the city, might be used to imagine the scale of Chicago and trace the vectors of lives lived there.

My memory of the sparrow returns to me from time to time, according to no schedule that I can make out. When it does, I understand it to remind me that life is short and you can’t do much about what’s coming, so there’s not much point in worrying about things. About all you can ask for is some minimal chance to square up to whatever’s on the way and perhaps try one last inspired escape move. Or you can choose instead to stand and face it like a sparrow.

That thought cues another memory, an aural one: the distinctive metallic clangor—NangNangNangNangNang—of the warning bells at railroad crossings along 71st Street in South Shore, where I grew up. The tracks run at grade down the middle of the street, and the bells start up at the approach of each double-decker commuter train or late-night freight that comes through the neighborhood. Gates drop too, but the sound, one of the very first I can recall hearing as a child, carries the message. It says Here is something huge and fast—beautiful and potent and remorseless, carrying a payload of the lives of others—that can take you places or wipe you out. It says Chicago. 


Carlo Rotella

Carlo Rotella is the author, most recently, of The World Is Always Coming to an End: Pulling Together and Apart in a Chicago Neighborhood. He is a professor of American Studies, English and Journalism at Boston College.

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