Well, get ready for the orgasm: as far as I'm concerned, Chicago has been damned near indistinguishable from Detroit for at least 20 years.
Well, I have to disagree. I've lived in Chicagoland as recently as 1999 and it is not NEARLY the shithole that Detroit is - though, I grant you, that there are areas in Chicago that do look like third world countries after Armageddon.
Daley was/is a crook, but he is a smart crook and he somehow held on by his fingernails. The various crooks that have fronted that seeping chest wound known as Detroit were too busy going to jail to be smart.
Detroit will hit the shitter before Chicago, that's for sure. But Chicago's headed there too.
It's a Rust Belt thing....