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I thought about your question, and I would actually argue Chicago is probably close to peaking right now; sure there are crime and corruption issues, but that is not unique to current Chicago, I'm not from Chicago, but seems to be business as usual. To my knowledge, the city has never been as wealthy, or with as many high paying jobs as it is now.
I think the biggest difference now is that other cities have caught/passed Chicago in several aspects. LA and NYC now have much safer cities (both in reality and perception), and regions such as Wash. DC and SF Bay Area are now wealthier (both on average and raw numbers), so while Chicago probably is enjoying more success than it ever has, it's no longer the next premiere city after NYC (arguably).
For me personally, the biggest thing holding Chicago back is still crime, not so much black on black violent crime on the Southside that Northersiders may or may not pay attention to on the news, but the spillover to good, family oriented neighborhoods. I live in what is arguably the best neighborhood for families in the city (West Lakeview/Southport Corridor), and the crime here is pretty alarming, and much higher than I ever anticipated. My garage has been broken into twice in the past 18 months, there was a armed robbery in front of my house (in broad daylight), there are literally robberies/assaults every weekend within a 2 block radius of my home, and to top it all off, there was a shootout yesterday 2 blocks from my home, where ~80 gunshots were fired. These are the issues Chicago should be most concerned with, violent crime in wealthy, family neighborhoods.
Cops know that the allocation of resources has become a nightmare -- the City cannot afford to fully staff every district. Tactical officers are being re-deployed to hotspots in a haphazard way. There is no real strategy to root out gangs, heck many alderman are tied in to gangs as a source of votes.
The rise in crime in "nice" areas is 100% due to fact that cops cannot be two in places at once -- crooks that see tactical officers swarming into neighborhoods in response to gang shootings of little kids know that those cops won't be around nice neighborhoods -- good time to steal some easy to fence tools from a garage. Toss in the need for cops to babysit "protesters" trying trash No. Michigan Ave and that makes it easier for crooks to grab iPhones & purses from folks on Halsted or Southport...
The mindset of "overwhelming force" that works in gang turf is going to backfire in neighborhoods where folks blithely stroll home from 5AM yoga before work or wanna take their miniature purse dog for a walk after watching Jimmy Kimmel...
There simply aren't very many podium buildings being built outside of the Central Area, and while downtown is critical to Chicago economically and is the most significant geographical region that currently ties Chicago into the Global economy, it has never really been the "soul" of Chicago. Places that are the soul of Chicago are being renovated/gentrified in a far more fine-grained fashion than the Central Area. Places like the Bungalow Belt, which have been closer to the soul of Chicago than downtown, are still around and, while changing, moving more slowly and less dramatically. The Central Area has always been Chicago's face to the world and region, not the heart and soul of everyday local Chicago.
Interesting perspective; and that is probably the mindframe many share have who applaud the new buildings going up. I may not be in Chicago to see it happen, but I often wonder what type of Central Area, as you put it, we will end up with once the area is built out, and the result is massive, block long developments with parking podiums, and precast concrete facades...
...The rise in crime in "nice" areas is 100% due to fact that cops cannot be two in places at once -- crooks that see tactical officers swarming into neighborhoods in response to gang shootings of little kids know that those cops won't be around nice neighborhoods -- good time to steal some easy to fence tools from a garage. Toss in the need for cops to babysit "protesters" trying trash No. Michigan Ave and that makes it easier for crooks to grab iPhones & purses from folks on Halsted or Southport...
^^This AND I believe the closing of the housing projects with the disburesment of some troubled residents with sketchy intentions has negatively affected many city neighborhoods. My Chicago friends have reported an uptick in robbery type crimes in formerly stable ethnic areas and they are not happy!!
Interesting perspective; and that is probably the mindframe many share have who applaud the new buildings going up. I may not be in Chicago to see it happen, but I often wonder what type of Central Area, as you put it, we will end up with once the area is built out, and the result is massive, block long developments with parking podiums, and precast concrete facades...
I don't like parking podiums for a variety of reasons, but functionally how are they different from the block-long warehouses that they have replaced? I think parking podiums are a symptom of too much parking, which creates congestion and provides a perverse incentive to drive out of a neighborhood instead of walk and spend money in the neighborhood, and I think that when they're designed poorly (as many from the last boom of skyscrapers between 1999 and 2010 were), they make the streets less visually interesting, but on a day-to-day basis I don't think they're any worse than the warehouses they replaced. Warehouses aren't interesting, don't bring in residents, and don't have attractive economic activity for the kinds of people drawn to the central area now.
Also, the term "Central Area" isn't my term - it's the City of Chicago's official term for planning. But since you don't live here, I guess there's quite a lot you don't know about the City of Chicago's planning, or about the experience of actually living here now.
I don't like parking podiums for a variety of reasons, but functionally how are they different from the block-long warehouses that they have replaced? I think parking podiums are a symptom of too much parking, which creates congestion and provides a perverse incentive to drive out of a neighborhood instead of walk and spend money in the neighborhood, and I think that when they're designed poorly (as many from the last boom of skyscrapers between 1999 and 2010 were), they make the streets less visually interesting, but on a day-to-day basis I don't think they're any worse than the warehouses they replaced. Warehouses aren't interesting, don't bring in residents, and don't have attractive economic activity for the kinds of people drawn to the central area now.
Also, the term "Central Area" isn't my term - it's the City of Chicago's official term for planning. But since you don't live here, I guess there's quite a lot you don't know about the City of Chicago's planning, or about the experience of actually living here now.
Thanks for the condescending reply, but I do live in Chicago, have for a total 4 years (in two different tours of duty), and am very invested in the city; I own or partly own 18 different properties within the city. You are correct though that I don't know the in's and out's of the city planning, or lack thereof.
Location: East Central Pennsylvania/ Chicago for 6yrs.
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Nice to see the thread has gotten CIVIL and a good conversation on things Chicago has done, can do and some things it can and could do better. Visitors and Tourist as I am basically today on visits again. Still are IMPRESSED with Chicago far more then not. Most have views they take home.... much better then expectations they came with.
This all still helps the city even when negatives are heard. I always post POSITIVES on the city as I've seen and read about. Especially as many negatives get posted sometimes.
I do not think taking all to political mocking and blame. Show any more corruption then Chicago had in virtually ANY past era. Whether from old movies like "In Old Chicago" before the Great Fire. Had Gambling King's with Political connections to the Capone and Mafia movies.
It seems to have ALWAYS been a TALE OF TWO CITIES. One of crime and wrong doers and the other who LIVED NORMAL WORKING LIVES IN A CITY THAT PROVIDED THEM. More a City that worked then not.
The way Downtown has been Restored and Much New infill and even many areas totally new skyscrapers. I find awesome.
Gentrified neighborhoods look great and I believe Chicago has some GREAT INFILL multi-story resident housing. Better then many other cities get. As for Podium-style High-Rises to Skyscrapers. Yes some perhaps could have been done better. Especially those first built in areas not much was in yet. But newer additions built around generally add more today. Some green-space and greener buildings and retail and eateries can be added.
I agree that western gentrification will come as the Garfield's even Lawndale's have a great stock of some Greystones, sadly too many lost and Apartment buildings and areas not with Bungalows. Streetviews show areas of improvements. Infill and worst blight all removed. Nothing like the 80s war-zone looking areas I saw in the 80s going from the suburbs to city on the West/Southside. Sadly crime and gang turf is the major issue.
I agree that the city's bungalow belt and 50s early 60s last growth periods of the city are part of its heart and soul too. These are the areas the GREATEST GENERATION BUILT and lived.
I complement these areas too and Chicago's choices as a city of Front set-backs to front-lawns and choice of a full alleyway system. Where it ran their ugly Power-lines and poles. BELIEVE ME, WHEN YOU LIVE IN CHICAGO THEN VISIT OTHER AREAS. See ALL THEIR POLES are in FRONTS OF NICE HOMES.... EVEN ON FRONT LAWNS. They STAND OUT. Garages too were a aspect MOST home owners could have. Because of these alleyways. Just gave them smaller back yards though.
Great Aesthetically pleasant neighborhoods with Green-space and Many times HUGE TREES THROUGHOUT is common. To the preserved and mane-made new Lakefront the city re-created.
I complement the city for removing its FAILED HOUING PROJECTS and removal of the Worst blight once the city was labeled for and the stigma still it has for some. The city also MADE SOME GREAT IMPROVEMENT CHOICES FOR DOẂNTOWN and NEW PROJECTS That also were aimed at INCREASING THE CITIES TOURISM. IT HAS SUCEEDED ON ALL FRONTS. EVEN SURPASSING HOPES IN SUCESS.
As for the city's debt. I DO BELIEVE it will get through it. It has a track record of ALWAYS DOING SO. I don't think it is in the Nations interest to have the city cut Police more in cost saving measures. NYC in its declines to Bankruptcy in the 70s. Showed what it can lead too when it did that.
Detroit's declines and White-Flight were far too severe and Bankruptcy was necessary. NYC DID GET A FEDERAL BAILOUT in Federal loans as they were called. ONLY AFTER A RELUNTANT PRESIDENT FORD WAS PRESURED...... EVEN BY BIG BUSINESS. But NOT BEFORE NYC was on the BRINK in not nearly debts but SKYROCKETED CRIME due to severe police cuts already.
Again NOT IN A NATIONAL INTEREST AGAIN if Chicago's cuts came and resulted it such increases far worst then now. Those that play the political card and Union blame. Still offer no solutions that avoid declines in vibrancy the city has gained last few decades and anything that will result in a greater increase in crime. Let NYC in the 70s be a means to not allow that much to come.
Seems like it will take the FEDS to step in and force some pension debts compromising. Then I believe SOME FORM OF GOVERNMENT LOANS.... as real loans or bailout as NYC got? To keep the city from a fall and threaten its successes and RISE especially crime that NYC saw in the 70s.
Something I would like to see.... if at all possible. From President Obama just before he leaves office. NO HATE PLEASE.... and Political blame game to take the thread into. But if SOMEONE DOES HAVE SOME SOLUTIONS that can still keep the city afloat and address the key issues..... pension debts? To the State level..... Surely that could be discussed.
But to say let the city decline....... I don't accept as anything close to a National interest or All Chicagolands's. Stipulations and requirements should be made in any government loans also. But LET'S NOT MAKE THE THREAD A POLITICAL BASH FEST BLAME GAME. SOME SOLUTIONS ??? Maybe.
The whole corruption reality and image is so old school now that one can still find the 1950s in Chicago; coincidentally 1950 was Chicago's population peak. Worse is the continued boasting about the ''Chicago way'' and ''welcome to Chicago'' response to corruption; wonder how many people still think that's funny with the catastrophic tab coming due for Chicago and Illinois.
The Daley Machine Redux (Little Richie) sure left a mess.
Chicago has always reached into its corrupt political establishment to ensure grease the gears of the Chicago Way. Bottom line: it's just not fun, interesting or entertaining anymore. The voters created and sustained this whole thing so, of course, they are not blameless in any of this.
Exactly! People try to own the corruption with bravado, which is foolish.
I think Chicago is headed towards a tactical bankruptcy to free itself from the pension woes. These will most likely be assumed by the state of Illinois in some attenuated fashion, and the hot potato will ultimately be grasped by voters in a constitutional amendment enabling pension cuts. Pension holders should not bank on receiving their (contractual) due in full - there simply isn't enough money.
I think Chicago is pursuing a Dubai strategy - transform transient income into lasting income by building edifices that attract people. For Dubai, that's oil money. For Chicago, that's public debt. Whether that's a good strategy stands to be seen, but Chicago has lasted this long while St. Louis, Detroit, Cleveland, and Milwaukee succumbed to urban decay.
Chicago may one day be the Comeback Kid, but it'll never be the Cincinnati Kid.
Some Great Lakes humor for you on this dreary day.
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To keep the city from a fall and threaten its successes and RISE especially crime that NYC saw in the 70s. 
On a lighter note
