U.S. City of the Year: Chicago

Skyscrapers, green roofs, and house music — a very American metropolis.

U.S. City of the Year: Chicago
Chicago Sun Time: In front of Anish Kapoor’s Cloud Gate in Millennium Park | photo illustration by Peter Funch Chicago Sun Time: In front of Anish Kapoor's Cloud Gate in Millennium Park | photo illustration by Peter Funch

In the bottom of the ninth inning of the 2005 World Series, as the long-suffering Chicago White Sox were about to win their first championship in 88 years, play-by-play announcer Joe Buck waxed eloquent about Chicago’s South Side, where the Sox play. He described it as “a collection of neighborhoods…Irish neighborhoods. Italian neighborhoods. Polish. Lithuanian. Firemen. Policemen. Schoolteachers. Stockyard workers.” Stockyard workers? The last stockyard closed in 1971. Irish, Italian, Polish, Lithuanian? The South Side has long been predominantly African-American, and most of its immigrants now are Mexican. Yet that is how many view the city, through a lens dominated by the past. If you travel abroad and tell people you’re from Chicago, they’ll often pull their hands out of imaginary holsters and start shooting. To them, the city is still Al Capone’s town, which it was — nearly a century ago.


The real Chicago isn’t so easy to keep up with. It’s constantly reinventing itself. Jumpy. Agitated. Impatient. It’s as if the place is trembling. Move aside. Don’t linger. And if you’re going to dawdle, get out of the way. But what any Chicagoan will also tell you is that the past is very much present. It doesn’t go away. It shouldn’t. In fact, that’s Chicago’s lure and its beauty: its ability to take what was and figure out what could be.

Consider Millennium Park. The city’s spectacular growth in the late 19th century was in large part because of the railroads. Chicago, centrally located, could ship anywhere and receive anything. But 100 years later, the railroads here had become near relics; the dozens of Illinois Central Railroad tracks that converged downtown, an eyesore. So what did Chicago do? It covered some 25 acres of tracks and commuter lines with a massive platform, one so sturdy that it could build a park on it. It made the park’s centerpiece a band shell, designed by Frank Gehry, that feels simultaneously whimsical (it resembles a tangled ribbon tossed by the Lake Michigan breeze) and brawny (that ribbon is made of steel, a call to the city’s past as a center of industrial might). Some 100 years ago, Daniel Burnham, who oversaw the construction of the 1893 World’s Columbian Exposition and drew a layout for the city that included putting everyone within walking distance of a park, declared, “Make no little plans.”

And so Chicago does not. FAST COMPANY has named it U.S. City of the Year, recognizing not its past but its present — and its future — as a place where there’s room to stretch. Chicago has given America social investing and the stories of Stuart Dybek and Aleksander Hemon. It has been greening itself since long before it became trendy, and it has been dancing, too — this is the home of house music, Wilco, and Lupe Fiasco. Here, in the birthplace of the American skyscraper, Santiago Calatrava is redefining the form with his Spire, while at the Art Institute, Renzo Piano is building a $300 million addition. The economy is growing faster than New York’s or L.A.’s. And one of Chicago’s own, who arrived in the 1980s and, in the tradition of the great rabble-rouser Saul Alinsky, took a job community organizing, has made a shockingly viable run for president, despite everyone telling him he was too inexperienced. Early in his campaign, Barack Obama told supporters, “I try to explain to people, I may be skinny but I’m tough. I’m from Chicago.”

Aware of all the writers who have come before — Carl Sandburg, Richard Wright, Nelson Algren, Mike Royko, Studs Terkel — I have no pretensions of having the last word on Chicago. Nor can I hope to capture in such a short space the contradictions of this place. Wright, who launched his career here, once wrote, “There is an open and raw beauty about that city that seems either to kill or endow one with the spirit of life.” I’ve written plenty on the former and so here want to dwell on the latter. Every time I set forth in this scrappy place, I’m reminded why, despite my roots as a New Yorker, I’ve chosen Chicago as home: Alongside the failed and the fragile, it’s a city of romance and optimism.

The people, of course, give a place its soul. So I visited with several Chicagoans who personify this city. They took me places that seemed at once to stay in place and move forward. Chicago is, after all, ever in motion, pulling from the past while pushing at the future.


Not long ago, a delegation from the International Olympic Committee was being bused around town, and its guide, Tim Samuelson, the city’s cultural historian and resident Boswell, sensed ennui. Or maybe it was skepticism. Regardless, given that Chicago is the U.S. nominee to host the 2016 Games, that was no good thing, especially to Samuelson, a hoarder of city artifacts — from smoke-stained ceiling pieces from the 708 Club, the premier blues joint of the 1940s, to Eliot Ness’s handcuffs — who once told me, “My whole existence is Chicago.”

Well, Samuelson begins to lecture those out-of-towners. He tells them how Chicago rose out of a mud hole, how after the great fire of 1871, many thought that was the end for the city, and then how the nation’s first skyscrapers rose, monuments reaching to the heavens. He recounts how in 1933, amid the Depression, the indefatigable city decided to get people to work and to provide a diversion from the hard times — and so built one of the all-time great World’s Fairs, themed the Century of Progress. And then Samuelson asks his travelers, “For God’s sake, why don’t you give us something tough to do?”

Samuelson, you might think, is stuck in the past. But he understands well how history informs not only the present but also all that lies ahead. He recently met me in the entranceway of the 104-year-old, 12-story Carson Pirie Scott department store, one of architect Louis Sullivan’s masterpieces. He directed my attention to the thick columns, topped by intricately ornamental capitals, which have the effect of flowers in full bloom. Samuelson noticed my awe and later told me that he was only 7 when he first saw the building, and he was mesmerized too. “With all these exotic forms just swirling all over,” he said, “it seemed alive.”

Sullivan, of course, helped lay the foundation for American modern architecture and did it here because there was no one to tell him to do it any differently. Samuelson is a Sullivan connoisseur. He’s working on an exhibit — along with graphic novelist Chris Ware — to celebrate Sullivan’s philosophy that buildings should be organic to their creators and to their place and time. He’s here today to consult with the architects who are restoring the building, a process that will take longer than its construction did.

For years, the city stood by as architectural masterpieces — among them, Sullivan’s Chicago Stock Exchange — were razed. But in part because of Samuelson’s protestations, there has been renewed interest in preserving and rejuvenating what’s left. In a rough section on the city’s west side, for instance, sits the Garfield Park Conservatory, a cavernous 4.5-acre greenhouse with lagoons and waterfalls, designed by the landscaper Jens Jensen. It had fallen into disrepair. Pipes had burst; windows had cracked. Then in 1994, the city began to revitalize it. In 2001, the Conservatory mounted a magical exhibition in which the artist Dale Chihuly planted glass flowers and lily pads among the nonglass trees and plants. It drew more than 500,000 people — and signified the city’s reconnection to a secret about hard-nosed Chicagoans: We’re a bunch of tree huggers. Just consider the motto on the city’s seal, URBS IN HORTO, or City in a Garden.


While the rest of the world contemplated global warming, the city revived that hothouse and planted trees along its streets and boulevards. Freeman maples. Bald cypresses. Kentucky coffee trees. Half a million altogether. At first, it was because the mayor wanted to doll up the city. But Chicago is ever practical, and there was the realization that this prettifying might serve a purpose. Thus began the greening of Chicago. Almost by accident.

City Hall now has on its roof a garden that boasts more than 100 plant species and that produces enough honey (500 pounds last year) to sell commercially. One day last summer, scientists measured the temperature on that green roof: It was 70 degrees, compared to a bubbling 152 degrees on the blacktop roof of the county building next door. Chicago has more than 80 acres of green roofs. Its 2,000 miles of alleys are being repaved with a permeable substance that will divert rainwater to Lake Michigan. And if you agree to build green, you can get an expedited building permit (three weeks, as opposed to what one architect told me is often six months), which gives new meaning to all things green making this city work.

When word got out in City Hall that Fast Company had selected Chicago as city of the year, I got a phone call from the mayor, Richard M. Daley (it does sometimes feel like a small town), son of kingmaker Richard J. Daley. The Daleys have ruled this city for 40 of the past 53 years. The mayor told me that at the annual mayors’ conference, other mayors grill him to learn what the city’s doing with its greening. “That’s all they want to talk about,” he said. He spoke proudly of an eco-friendly SRO designed by Helmut Jahn that, among other things, collects rainwater to flush the toilets. Another renowned architect, Stanley Tigerman, designed the new Pacific Garden Mission, a refuge for the homeless (1,000 at a time) that has greenhouses where they compost. The mayor, a regular biker, is considering a program he saw in Paris: the creation of a public fleet of bikes. Now, that would be a test for Chicago.

Once a month, Tony Fitzpatrick and Kelly Hogan lunch together at Hot Doug’s, which, if not the best, is certainly the most upscale (upscale being relative) of the city’s famed hot-dog joints. The fare ranges from your traditional dog — in Chicago, that means with mustard, onion, sweet-pickle relish, tomato wedges, peppers, a dash of celery salt, all topped with a pickle — to a special game sausage (this week, it’s elk). On Fridays and Saturdays, you can get fries cooked in duck fat.

Tony, an old friend, is an actor, raconteur, deejay, and artist. His boisterous collages, some of which are in the Art Institute’s collection, are on exhibit through July — “The Wonder: Portraits of a Remembered City,” the show is titled — at the city’s Cultural Center. In these collages, Chicago’s lives, moods, and politics collide; he once told me, “This place gets in your bones and ruins you for anywhere else.”


Over the years, he has also told me about Hogan, a singer whose voice, Tony says, “makes me see colors.” So the three of us spent a lunch hour at Hot Doug’s talking music, much of it about a band Hogan sings with, the Struts. It’s a collection of musicians who play in at least 20 other bands, including Poi Dog Pondering (alternative, with touches of Polynesian and house) and Wilco (indie rock/alt-country). That’s Chicago, a city that pushes boundaries, a city where genres hold little sway. A punk rocker from Wales once declared that he avoided L.A., because there they talked about whom they were going to play with; and he avoided New York, because there they talked about the projects they were going to do. In Chicago, he said, they come to work — without regard for what others might think.

One recent evening, Hogan met me at the Hideout, where she bartended for more than nine years and still sometimes performs. It’s hidden in a small industrial corner on the north side, so when Hogan gave me directions, she instructed me to go over the river, past the railroad tracks, across the street from the city’s fleet of garbage trucks. If you get to the old U.S. Steel plant, you’ve gone too far. She paused. “I guess it’s a good place to bump somebody off,” she laughed.

The Hideout is a wood-framed house built at the turn of the last century, probably by squatters, when the neighborhood was mostly working-class Irish. After prohibition, the downstairs became a drinking hole for steelworkers. In 1996, it was purchased by four partners who did little to change the look — photos of the original owners, Angelo and Phil, still hang over the bar — but brought in musicians. The thinking was that musicians could experiment here, and they have; on any given night you could stumble upon a jazz quartet or a rock band or a folk singer. Neko Case played the Hideout before winning wide acclaim. Fiddler/violinist Andrew Bird worked his way from swing to indie rock here. And when the Frames passed through town, Glen Hansard and Markéta Irglová used the place to test some songs they were writing for a little movie called Once — one, “Falling Slowly,” won Best Song at this year’s Oscars.

One of the Hideout’s owners, Tim Tuten, told me, “We’re conscious of what made Chicago great. We have a historical reputation to uphold. This is the city of Sam Cooke, Curtis Mayfield, Lou Rawls. It’s from the ground up.” It was past midnight, and Tuten, who speaks with the drive of a Hendrix guitar riff, expounded on the 1893 Columbia Exposition (The Devil in the White City made everyone feel like an expert on it) and the time Wilco played at one of their block parties (kick-ass block parties being a city tradition) and how he recently discovered that in the 1960s Nelson Algren would down a beer at the Hideout. On the drive home, I listened to a CD Hogan had burned for me. She’s singing covers — from Allen Toussaint to the Violent Femmes. Her voice, rich and eclectic as the city’s neighborhoods, wanders throughout an exhilarating range. As Tony Fitzpatrick once told me of Chicago, “It’s a place that allows you to run.”

Calvin Holmes suggested we meet at 10 on a Saturday night at Cuatro, a Latin-Caribbean restaurant owned by a young Chicagoan whose dad, a Mexican immigrant, delivered meat to bodegas around town. We weren’t there to eat, but to hear house music. Holmes considers himself a “househead”; he often plans his weekends around finding good house in Chicago.


Holmes — 43, lanky, open-faced — came to Chicago from East St. Louis, Illinois, to make something of himself. His grandmother had warned, “If you can’t make it in Chicago, you can’t make it anywhere.” Holmes made it just fine. He arrived shortly before Harold Washington’s 1983 mayoral campaign against an opponent whose slogan was “Before it’s too late,” a not-so-thinly-veiled plea to white voters. “I remember thinking, Where is all this hate coming from?” Holmes told me. He got an internship in the administration of Washington, who, in addition to being one decent man, was an avid reader, so Chicago’s main library is named for him. “This is a place where black folks have taken stock of themselves,” Holmes said. “They’ve come through this crucible. And folks felt like we could do stuff now, we could make things happen, that finally there’s some equity in this town.”

Holmes now runs the Chicago Community Loan Fund, which does what he calls “opportunity finance” — making low-interest loans for commercial development in low-income neighborhoods. It’s the equivalent of a nonprofit poker player (a “rounder,” as they were once called), willing to wager on what may at first not seem a winning hand. Chicago is the epicenter of social investing — making the market work where it hasn’t. It began with Shore Bank, the innovative lender that helped inspire Muhammad Yunus, who, with his Grameen Bank, was awarded the 2006 Nobel Peace Prize.

Holmes’s operation is small — under $5 million in loans a year — but it has had a terrific impact, including winning Illinois’s first green-housing award for its investment in renovating a dilapidated brick apartment building in the Woodlawn neighborhood. The group has funded a building for artists, the restoration of tenements, and a soon-to-be retail center, all geared toward people who need a foot up. “When I think of Chicagoans,” he told me, “I think of people who are straightforward, not pretentious, and fair on balance. You’re smart, you work hard, you’re decent, you’re good — we’ll take you in.”

Holmes showed up at Cuatro in a dark suit, having just come from a Lyric Opera performance of Tchaikovsky’s Eugene Onegin. “I need a good drink,” he told me, so we ordered beers. He then excused himself to say hello to the deejay, DJ FLX (real name: Felix Cuevas), who came to Chicago because you have to pass through the city if you’re going to make it in house — though it’s now more popular in Europe and Japan.

House was pioneered here by the legendary deejay Frankie Knuckles, who, along with roughly 1,100 other Chicagoans, has a street named for him. (This city likes to honor its own.) Not unlike the blues before it, you can hear house in small venues around the city; and every July 4th weekend in Jackson Park (where Clarence Darrow’s ashes were scattered), there’s a picnic at which thousands spin and undulate to various deejays mixing their funk.


DJ FLX, just back from touring Morocco and Paris, began playing a set accompanied by the trumpeter Kafele. FLX’s style is “deep house,” a uniquely Chicago sound with a profoundly soulful, I-dare-you-to-sit-still pulse. As Holmes dances, he tells me he has a spot in the city that feels as spiritual to him as house music. It’s an outcropping on Lake Michigan, just off 39th Street, an unusually quiet stretch of the 29-mile public lakefront. Holmes often walks out on this spit of land and admires the graceful yet muscular skyline, a mixture of old and new, works of art mingled with feats of engineering. “It’s so radically vertical,” he says. “Shooting up from the flat lake and flat land, it seems to point to the future.” Indeed, the cityscape is constantly morphing; its newest marvel is the Chicago Spire, a 150-story corkscrew that’s under construction. According to Calatrava, its architect, it’s meant to resemble a plume of smoke rising from a campfire Native Americans would have built centuries ago on the banks of the Chicago River.

I soon realize that I too am dancing in place. Holmes doesn’t notice. His body is under sail to the beat-driven winds of FLX’s mixes, but his mind is still on the skyline and the 8-mile walks he often takes from his office to his home. The stroll takes him to the outcropping and through Bronzeville, a neighborhood once known, like New York’s Harlem, as a center of black commerce and culture. Holmes has done some financing in that community, which is undergoing radical change, mixing old and new, including a Sullivan-designed church Tim Samuelson is helping to restore (on hands and knees, Samuelson collected more than a thousand shards of glass after a devastating fire so that the stained-glass windows could be replicated) as well as mixed-income developments rising where the world’s largest stretch of public housing once stood. “In Chicago,” Holmes says, “it’s happening, right in front of your eyes.”

Alex Kotlowitz is the author of Never a City So Real: A Walk in Chicago.