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Chicago and Its Future: A Glass Half Full

America’s third-largest city has a plenitude of problems. But it has great advantages as well.

The downtown Chicago skyline at sunset.
Downtown Chicago.
(Rudy Balasko/Shutterstock)
Moving to Chicago after college changed my life. The city changed this kid who grew up four miles outside a town of less than a hundred people into an “urbanophile” — a name I gave to a blog I later started. So I’ve always had a special attachment to the city.

My move to Chicago in 1992 coincided with the decade in which America’s urban resurgence exploded. Waves of redevelopment surged outward from the downtown Loop and the thin north lakefront gentrified zone. A dingy industrial city was cleaned up and adorned with flowers, a reclaimed river, wrought iron and classy streetlights. The vibe of the city transformed from The Blues Brothers to Ferris Bueller’s Day Off. Richard M. Daley was heralded as one of America’s supermayors.

The city’s path proved to have downs as well as ups. The 2000s turned out to be a lost decade of job growth in which Daley seemed to have lost his magic touch. The city dug itself into a financial hole that would only become apparent later. Still, the young college grads of the Midwest kept rolling in, and ultimately so did business. The 2010s, though not without challenges, saw another business surge into the city, as United Airlines and Boeing and other corporations planted their flag in downtown Chicago. ConAgra and Molson Coors were drawn to the city from out of town. Big tech set up shop and the city’s startup scene grew.

In the last few years, the city has again hit choppy waters, with many raising questions about its future prospects. Crime, a problem that unlike in New York had never fully been conquered, has come back to the fore. Carjackings, shootings, and industrial-scale shoplifting now plague even the most upscale areas of town. Most workers are still not coming into their downtown offices. Upscale Michigan Avenue has seen significant retail closures. And, especially ominous, several major corporations have recently announced their departure from the region: Boeing, Caterpillar, and the hedge fund giant Citadel.

Yet despite the gloomy headlines, there’s a lot of reason to feel that Chicago has a basically bright future. The city remains home to a large and diverse collection of major corporate headquarters. Food giant Kellogg’s recently announced it will be moving the headquarters of its largest business to Chicago after the company splits up. The city is a huge center of professional services in law, consulting and accounting.

Despite the departure of Citadel, Chicago will remain an important financial node so long as the CME Group, the world’s most important financial exchange, remains in the city. O’Hare Airport remains a key national hub, and the region a critical logistics center in general. The University of Chicago and Northwestern University are nationally prominent. In short, Chicago retains a powerful collection of economic assets.

The city is also physically beautiful, with a magnificent lakefront setting. In a country with precious little genuine urbanism — dense, walkable, mixed-use neighborhoods and extensive transit — Chicago has all of that. And its urbanism comes at a price unavailable elsewhere. With the city’s real estate values having lagged since the Great Recession, and urban real estate prices in other Midwestern cities having soared, the city is now actually one of America’s bargains on a quality-price ratio basis. It’s still possible for a professional couple to buy a decently spacious condo with enough room for a family, and with a parking spot to boot. This is unachievable for all but the rich in New York City.

And while much of the Midwest remains stagnant, the region as a whole still is large and important. Chicago is its capital, and that is not going to change. For a large number of the Midwest’s educated young people, Chicago will remain the preferred destination. Midwestern tourists will visit the city for shopping and entertainment. Midwestern cities and states will look to Chicago for high-level business services.

That’s not to say all will be well. The city never was able to fully transform itself into a coastal-style elite metropolis. Realistically, Chicago’s global city dreams and ambitions are on hold. Both the city and state are bedeviled by poor leadership that seems in over its head and incapable of dealing with the serious problems facing both. Even its once vaunted business leadership has lost a step. But despite the problems, there are so many assets and forces sustaining Chicago that this metropolis will remain a nationally powerful and prominent city for many more years to come.

Governing’s opinion columns reflect the views of their authors and not necessarily those of Governing’s editors or management.
An urban analyst, consultant and writer. He can be reached at or on Twitter at @aaron_renn.
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