Well, the infrastructure has only improved in Chicago in recent decades, so I haven’t seen that effect. The city has budget problems, but those are mostly all due to the union demands and bloated pension plans, not from drops in revenue.
One thing that helps Chicago is that the near suburbs are in Cook County, so a lot of suburbanites are paying into the same property tax pool. Also, most of the jobs are still in the city, so those businesses are still paying taxes.
I see; here in NJ our municipal taxes pay most of the expenses. The union demands and pensions are killing all of NJ; the cities are dying faster because those expenses are so much higher.