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Ups and Downs - Spring 2022



What’s Ahead for Chicago?

I’ve thought a lot about the future of Chicago since moving to Madison and swapping my Land of Lincoln license plates for new ones with America’s Dairyland on them (I still can’t quite get used to that).

I know many would look at the plain fact of my move north and conclude that I’ve become a pessimist about Chicago and have voted with my feet. That’s not an unreasonable conclusion, and it’s certainly more right than wrong.

At the same time, my feelings about what had been my chosen home town since my late 20’s are pretty complex, and it would be unfair to say that I’ve completely written off the city, even though I am no longer a citizen of Illinois.

I do think that the city is in for at least a few more rough years following what can only be described as an underwhelming start to the 21st Century. Since 2000, the Chicago area has consistently under-performed its peer group of major metros, and the city and regional populations have barely budged while other coastal and Sun-Belt cities keep growing.

To take just one example that I still can’t quite wrap my head around, Brookfield Properties recently announced that they were handing back the keys to Water Tower Place, a completely unimaginable possibility only a short time ago. Water Tower has long been regarded as the trophiest of trophy properties, one that investors boast of owning and pay up for the privilege. If Brookfield is now walking away from Water Tower Place, what does that say about the future of the rest of the city?

Yes, young people are still coming to Chicago from Big Ten schools upon graduation every year. But many of them don’t seem to stay for very long. Many others are just bypassing Chicago completely for the hipper and buzzier cities we keep hearing about.

This inauspicious start to the 21st Century took a turn for the (very much) worse with the pandemic and aftermath of the murder of George Floyd. By just about any measure, Chicago today is worse off than it was just a few years ago – increased crime, decreased livability, diminished downtown vitality and tattered reputation.

Any of these problems, individually or in some combination, could yet push Chicago over the edge and send it into permanent decline. And yet, there are signs that the city could still get its act together, get through this brutal time and emerge on the other side a better place.

There are a couple of things I’m seeing that give me hope that Chicago’s best days are not, in fact, behind it. Did you know that the South Side Lakefront neighborhoods – from the South Loop all the way to South Shore and the Indiana border – are almost without exception seeing population increases for the first time since the middle of the last century? With the exception of Woodlawn, every South Side Lakefront neighborhood saw population increases between 2010 and 2020, several of them by double-digits.

Even in Woodlawn, which did register a small population decline, a lot of good things are happening with the imminent arrival of the Obama Presidential Center and all the new development that is taking place in the neighborhood. I think there is a real possibility that Woodlawn, and other South Side Lakefront neighborhoods, are just on the cusp of a revival that will catch many by surprise. Things are truly looking up on the South Side, at least for those neighborhoods with proximity to Lake Michigan.

Downtown, the Fulton Market corridor is simply unstoppable (good thing, since the Mag Mile seems to be in terminal decline). Even during the depths of the pandemic, when the rest of the Loop looked like a ghost town, Fulton Market keep humming. True, Chicago is not yet (and may never be) the next tech behemoth. But does it need to be? Increasingly, Chicago has been attracting back offices for a slew of tech companies based elsewhere. These companies are increasingly drawn to Chicago for its (relatively) low cost of living and deep pool of talented and highly trained workers.

If enough of these companies hire enough tech workers in Chicago, it’s not hard to imagine that Chicago could actually emerge as its own tech mecca and claim more of that business from the coastal cities that currently dominate the sector.

One last reason to believe the future of Chicago can still be better than the past. There is no majority in Chicago – a city with roughly equal numbers of people of European, Latin American and African heritage, and a surging population of people with roots in South and East Asia. All of this makes Chicago a more interesting and diverse place, something I believe will serve the city well in future years.

For all the friction that can erupt between these groups, attitudes are changing. Many Chicago area residents, particularly those under the age of 40, genuinely love living in a city of such incredible diversity and appreciate the cultural richness that this diversity brings. The city’s long history of segregation is not over, but it does seem to be softening around the edges. I’m very optimistic that greater integration of our diverse populations is coming, and that the city and suburbs will be better as a result. This is happening all around Chicago (think Bronzeville for one notable example) and is bound to spread further with time.

I want to believe that a resurgent South Side Lakefront, booming Fulton Market corridor, diverse population and revitalized core can make up for the huge challenges we have faced in recent years. I don’t know if all of these positives can jell into something with enough momentum to overcome our many problems. Even if they do, I’m not sure I will live long enough to see it.

But one thing I know. Chicago is a great city – truly one of the greatest. I can’t give up on the belief that the region can overcome this awful period we are living through with a little time, a little luck and some serious hard work. I will be paying attention, even though I now live in another state. I plan to be a frequent visitor. Nice that I’m just a two and a half hour drive. When I miss Chicago – which is often – I know I can get back quickly.




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