While I am a certainly familiar with and have been to Chicago; I'm loathe to pretend some level of expertise in assessing the region's demographic/economic challenges.
That said, I did a quick scan online of news pieces and academic work using terms such as Chicago, Decline, Stagnation etc. to see what turned up and gave them a quick skim.
Lets start at the high level. The Region's population is not in collapse, but is flat to declining.
The City is not unhealthy when measured at the macro level, so much as it isn't booming and has something of a brand-image, and maybe a self-image issue.
There's no question that there has been growth in The Loop/DT Chicago area; and material decline in more challenged areas of Chicago, particularly on the south side.
Is violent crime an issue? Probably, at the margins, in as much as many (not all) of the areas seeing the steepest declines also have inordinate crime.
But that's almost certainly too simplistic an analysis. It would beg questions as to why residents aren't migrating from a higher crime area of Chicago to a lower crime one; and why more prosperous, lower-crime areas of Chicago aren't attracting sufficient overall growth to offset any losses. I don't think one can discount problems with crime, or bad schools or the like as having an impact, but there is surely more at play.
I saw some online discussion about the fact Chicago is merely mirroring Illinois as a whole; which is seeing state-wide population losses. I think that's important to the extent its true, because when you think of booming City's California in the recent past, or Texas or Georgia now, you're thinking of places where the State as a whole is seeing positive growth. Granted, that growth is often driven by the Alpha City or Cities of said states, and same would likely be true of Chicago and Illinois.
However, I also saw indications, that state-wide, Illinois has inordinately high property taxes, as well as higher sales taxes than many other U.S. States. That would seem to have some potential impact; though, again, my instinct is that overall, this is at the margins.
I say that, because many of the most desired, high-growth cities over the last few years, both in the U.S. and globally are high-tax or higher-tax jurisdictions, the thing is, there were another positive factors favouring growth that made those penalties worth paying.
It would seem this was less true in Chicago.
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If I had to take a guess, and I'd look for input from others more knowledgeable about the region than I......
I would say that:
1) The region is not heavy into the tech industry or other recent high-growth sectors.
Very similar to Toronto in its 1980 economic composition (Toronto was a centre of heavy industry) as those those jobs declined both due to the shifting of jobs to Mexico/China etc.; but also due to modernization of equipment, Toronto shifted gears, to become a financial services and tech. hub. Chicago may not have had the latitude to do the former (given the presence of NYC) but surely could have done the latter.
I noted much online discussion that state-subisides in Illinois and city-subsidies in Chicago were inordinately geared to subsidizing aging corporate giants like Sears, rather than fostering growth in new and emerging sectors.
I think its important to consider that while people may move for lower crime or cheaper property, one of the most common reasons to move is for a job.
If financial services and tech are growing sectors, you think NYC, Boston, The Bay area, and Austin, in the U.S. and Toronto and Vancouver in Canada.
Chicago isn't front and centre in that conversation.
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I think a big factor is likely median educational attainment.
When I look at Austin, for instance
I see a rate of 92% high school attainment vs 86% in Chicago. While we also see 50% with a Bachelor's degree vs 44% in Chicago.
I would tend to think that's reflective of population ready for employment in higher growth sectors, which in turn is indicative of whether those sectors will choose to locate/grow in Chicago.
That's just a thought.
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An environmentally conscientious, libertarian inclined, fiscally conservative, socialist.
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