General corruption/waste is another matter. Recycling in Chicago right now is notably inefficient, for example (something like a 9% clearance rate).
That's not really the question, though. The question is if you'd be surprised if they didn't.
I wouldn't be that surprised to hear that Chicago was unable to clear snow from a 100-year snow event because the funds were mismanaged or something similar. That sounds entirely within character.
I wasn't surprised when I heard about the ongoing problems with the Texas power grid, either. I was horrified by the deaths, of course, but did it surprise me that an for-profit utility market didn't result in a robust infrastructure? No. Infrastructure and utilities don't work well under those sort of economic pressures. I wasn't surprised it was fragile.
Former Mayor Michael Bilandic famously lost reelection in 1979 after botching snow removal following the large blizzard of that same year. Ever since, snow removal has been one of the city government's core competencies; even the quite intense Groundhog Day blizzard of 2011 was well-handled, though it managed to shut down LSD for a bit. There's plenty of mismanagement and corruption in city government to go around (the police department is famously corrupt and incompetent and shows no signs of turning that around), but snow removal is one thing that can generally be counted on here.
I guess if you’ve never lived near Chicago or visited in the winter, that might be reasonable. But they take snow extremely seriously. Like so seriously it’s funny. It truly is. The “mismanagement of funds” is true - they spend a lot of money on snow management.
They have over 200 snowplows, and every single garbage truck has a plow attachment so it can be put into plowing service, most of the city pickup truck fleet as well, etc.
[1] > Department of Streets & Sanitation (DSS) coordinates Chicago's snow and ice control efforts from Snow Command. This high tech command center allows us to access and view a network of cameras and pavement sensors to get a quick and accurate assessment of our pavement conditions citywide. We track incoming weather systems via Doppler radar and through constant communication with our meteorological consultants and the National Weather Service. And we combine all of these technologies along with the Global Positioning Systems (GPS) on all of our trucks to strategically deploy our snow personnel to up to over 280 snow routes.
People used to claim that the streets that alderman lived on got plowed first whenever it snowed, so the city put GPS on everything and built a plow tracking website, so you can see where everything is in realtime, any time it snows. [2]
[1] https://www.chicago.gov/city/en/depts/streets/provdrs/street...
[2] https://www.chicago.gov/city/en/depts/streets/supp_info/plow...