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My Chicago Part of the Places of a Lifetime series from Traveler magazine

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By Bob Greene

“‘The City that Works’ still does—and stays true to itself.”

Visitors to Chicago almost invariably return to their hometowns full of wide-eye praise for the place they’ve just been. Chicago, they say, is …

Well, they use a lot of words. They’re always surprised—that’s the word that comes up most often. Surprised by how huge yet paradoxically life-sized it is, surprised by how alive its downtown is (actually two downtowns—the Loop and North Michigan Avenue), surprised by how many things there are to do late into the night, surprised by how much more human it feels than New York, how much more authentic than Los Angeles.

All of that is true—but it doesn’t explain why Chicago is like nowhere else. And the reason for that is deceptively elementary. During the reign of the first Mayor Daley—Richard J. Daley, the father of the current mayor Richard M. Daley—Chicago was routinely described as “The City that Works.” It was a slogan the first Mayor Daley enthusiastically endorsed. At a time when cities all over the United States seemed to be falling apart, with no one able to stop their decline, Chicago, it was said, always seemed to operate smoothly.

But “The City that Works” is not the right phrase to describe what makes Chicago stand alone these days. Rather, the secret is a turn on that phrase—the secret is the fact that Chicago is a working city. A city that really is one.

Across the U.S., many cities appear to be striving to become urban theme parks—cities as concepts, cities as come-ons. They’ve given up—they know that the suburbs have won, and that the people aren’t coming back. So they dress their downtowns up like a traveling carnival—weeklong festivals, gimmicky food-and-shopping malls, special “nights”—in the hopes that the people who have moved away will occasionally make a brief return if the cities act like country fairs.

Chicago is not a fair, and it is not a concept. It is what it always has been: a city. A true one—and maybe it will be the last one standing. Visitors are welcome, but not necessary. Those elevated tracks aren’t for show—they are what they appear to be. That roar from the trains isn’t piped-in sound effects—it’s there every day and every night. Wrigley Field isn’t some cute marketing idea, some “retro” structure built to lure the nostalgic—you’re in a North Side neighborhood, and then suddenly you come upon the famous Wrigley, and a block later you’re back in a neighborhood. The lakefront, crowded with people all summer long, is no Disney project—Lake Michigan lapped up against this area long before Walt Disney or any other human was here.

Chicago is a city—that’s what startles visitors. They might not realize what it is that has left them wide-eyed. But they go home, to places that feel like pale echoes of something they once may have known (or heard about), and they try to describe what it is about Chicago that was so intoxicating … and they can’t quite put it into words.

They’ve been to a city. They’ve almost forgotten what that means.

BOB GREENE, former Chicago Tribune columnist, is author of And You Know You Should be Glad and Once Upon a Town: The Miracle of the North Platte Canteen.

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