Chicago: The City Where America Tested Itself

By Cliff Potts, CSO, and Editor-in-Chief of WPS News

Baybay City, Leyte, Philippines — July 9, 2026

Chicago is still my hometown. It treated me rough, and I still love it anyway. That is not sentimentality. That is the truth. It is a hell of a place to be from. The only reason I am not still there is simple enough: I cannot afford to live there anymore. Chicago got too damn expensive for me. That does not change what the city is. It just means the city I love is now priced like a club I can no longer get into.

And that pisses me off.

It also breaks my heart.

Still, love is love, and Chicago earned mine the hard way.

People who do not understand Chicago usually talk about it in one of two stupid languages. Either they talk about it like it is a war zone, which tells me they have been watching too much television and not enough reality. Or they talk about it like a tourist brochure, all skyline and deep dish and summer festivals, as if the city exists to decorate somebody else’s weekend. Both versions miss the point.

Chicago matters because it was one of the places where the United States worked its future out in public.

That is the argument.

After the Great Fire of 1871, Chicago rebuilt at a speed and on a scale that helped define what a modern American city could be. The fire killed about 300 people, destroyed roughly 17,450 buildings across nearly 3.5 square miles, and left nearly 100,000 people homeless (Encyclopaedia Britannica, 2026a). A lesser city might have spent a generation mourning itself. Chicago did what Chicago does. It rebuilt, and in rebuilding it pushed itself toward a new kind of urban ambition.

A few years later, Chicago helped give the world the vertical city. The Home Insurance Building, completed in 1885, is widely treated as the first tall building supported by an internal iron-and-steel frame and is generally considered the world’s first skyscraper (Encyclopaedia Britannica, n.d.-a). That is not trivia. That is Chicago helping write the grammar of modern urban life.

Chicago’s rise was not built on poetry. It was built on rails, trade, labor, slaughterhouses, grain, steel, and nerve. By the late nineteenth century, the city had become the rail and commercial hub of the interior, and by 1890 its population had pushed past one million (Encyclopaedia Britannica, 2026b). Between 1890 and 1982, Chicago was second only to New York in population, which helps explain the city’s size, swagger, and permanent chip on its shoulder (Encyclopaedia Britannica, 2026c).

That is why Chicago, and not just New York, has such a strong claim on American modernity. New York was and is a great city, but it carried old-world habits with it: Atlantic commerce, finance, inherited prestige, and a sense of itself as the front door. Chicago felt different. Chicago felt like the republic’s engine room. It was aggressive, expanding, inventive, ethnic, industrial, and not especially interested in apologizing for any of that (Encyclopaedia Britannica, 2026c). If New York looked back across the ocean, Chicago looked across the continent and tried to build the future out of smoke, steel, grain, freight, and audacity.

That is also why the World’s Columbian Exposition mattered so much. In 1890, Congress granted Chicago the right to host it, and when it finally opened in 1893, the fair drew about 25.8 million visitors during its six-month run (Encyclopaedia Britannica, 2026b). Chicago had beaten out rivals and then used the fair to announce that the city that burned was now fully capable of staging industrial modernity for the world to see. That was not just civic bragging. For once, the bragging was justified.

But if you want the real Chicago story, you cannot stop with the pretty parts.

Chicago is not great because it was clean. Chicago is great because it held the contradictions of modern America in one hard, loud, unforgiving place. Wealth and labor. Innovation and exploitation. Beauty and corruption. Vision and brutality. The city gave us the skyscraper, yes. It also gave us some of the defining labor battles in American history.

Chicago workers were central to the 1886 fight for the eight-hour day, with roughly 88,000 workers in 307 separate strikes in the city that year, and Haymarket became one of the defining labor flashpoints in the country’s history (Encyclopedia of Chicago, n.d.-a). Then came Pullman. The Pullman Strike began in May 1894 after wage cuts and spread into a national rail crisis, showing in plain daylight what happened when labor collided with capital and the federal government chose order over justice (Encyclopedia of Chicago, n.d.-b; National Park Service, 2025). Chicago was where the country tested how much democracy working people were actually allowed to have.

Chicago was also remade again and again by the people who arrived there. Irish, German, and Scandinavian immigrants began pouring in during the 1840s. By 1850, more than half the population was foreign-born. Later arrivals came from Italy, Poland, Russia, Ukraine, Greece, Lithuania, Bohemia, China, and elsewhere, entering through neighborhoods just northwest and southwest of downtown (Encyclopaedia Britannica, 2026d). Later still, wartime labor demand and federal immigration restrictions helped draw tens of thousands of African Americans from the South during the Great Migration (Encyclopaedia Britannica, 2026d). Chicago did not become modern by staying the same. It became modern by absorbing wave after wave of people and conflict and forcing them into one urban metabolism.

So when people reduce Chicago to lazy decline talk, or sneering crime talk, or the usual suburban panic nonsense, they are flattening one of the most important cities this country ever produced. Chicago was the place where the United States tested itself. It tested whether industry could scale. It tested whether labor could fight back. It tested whether architecture could rise higher. It tested whether migrants and newcomers could become the city. It tested whether power would modernize democracy or simply refine the machinery of control.

Sometimes Chicago passed.

Sometimes it failed magnificently.

But it never sat still.

That is why I love it. Not because it was kind. It was not kind. Not to me. Not to a whole lot of people. Chicago can be harsh, expensive, indifferent, arrogant, and mean as hell. It can also be brilliant, funny, resilient, and more alive than cities that are far easier to live in. That is the deal. You do not love Chicago because it flatters you. You love Chicago because it has force.

And yes, if I ever had the money and the reach to do something half-crazy and halfway perfect, WPS News would have a small office in Printer’s Row. That is where it belongs. After Dearborn Station was completed in 1885, Printer’s Row became the printing center of the Midwest, and today the neighborhood is still identified with South Dearborn between Ida B. Wells Drive and Polk Street (Encyclopedia of Chicago, n.d.-c; Choose Chicago, 2025). That neighborhood is not just real estate. It is print history. Ink, paper, machinery, freight, deadlines, and the hard romance of words made physical. If WPS News ever planted a flag in Chicago, that is where I would want it. Not some polished glass box trying to impress bankers. Printer’s Row. Put me near the ghosts of printers, editors, typesetters, and ink-stained hands. That would make sense.

Maybe that is all nostalgia. Fine. I have earned a little nostalgia.

But it is not only nostalgia. It is lineage. Chicago helped make me. The city gave me part of my edge, part of my anger, part of my humor, part of my suspicion, part of my refusal to bow down when somebody in a suit tells me to accept the official story, and part of the way I have been thinking about the city for years, even when I was writing about it in rougher form and rougher verse (Potts, 2013). Chicago was built by people who pushed freight, set type, packed meat, laid track, worked shifts, fought bosses, made deals, broke rules, built neighborhoods, and kept going. That is a hell of an inheritance.

And for all the damage the city did me, I would still rather be from Chicago than from almost anywhere else in the United States.

That is the truth.

Chicago is still my hometown. It treated me like shit, and I still love it. It is a hell of a place to be from.

I’m just not rich enough to live there anymore.

This essay is written by Cliff Potts, Editor-in-Chief of WPS News. WPS News has been active in one form or another on the internet since 2009; for more information, visit https://cliffpotts.org

If this work helps you understand what’s happening, help me keep it going: https://www.patreon.com/cw/WPSNews

References

Choose Chicago. (2025, September 6). 40th annual Printers Row Lit Fest. https://www.choosechicago.com/event/40th-annual-printers-row-lit-fest/2025-09-06/

Encyclopaedia Britannica. (2026a, March 12). Great Chicago Fire. https://www.britannica.com/event/Chicago-fire-of-1871

Encyclopaedia Britannica. (2026b). Chicago: History. https://www.britannica.com/place/Chicago/History

Encyclopaedia Britannica. (2026c). Chicago. https://www.britannica.com/place/Chicago

Encyclopaedia Britannica. (2026d). Chicago: People. https://www.britannica.com/place/Chicago/People

Encyclopaedia Britannica. (n.d.-a). Home Insurance Company Building. https://www.britannica.com/place/Home-Insurance-Company-Building

Encyclopedia of Chicago. (n.d.-a). Strikes. https://www.encyclopedia.chicagohistory.org/pages/1211.html

Encyclopedia of Chicago. (n.d.-b). Pullman strike. https://www.encyclopedia.chicagohistory.org/pages/1029.html

Encyclopedia of Chicago. (n.d.-c). Printer’s Row. https://www.encyclopedia.chicagohistory.org/pages/2481.html

National Park Service. (2025, January 10). A brief overview of the Pullman story. https://www.nps.gov/pull/learn/historyculture/a-brief-overview-of-the-pullman-story.htm

Potts, C. (2013, May 28). Chicago: From the past through tomorrow. WPS News. https://wps.news/2013/05/28/chicago-from-the-past-through-tomorrow/

David Wilson from Oak Park, Illinois, USA, CC BY 2.0, via Wikimedia Commons