Detroit went Detroit b/c it never even tried to evolve into anything other than the birthplace of the auto industry.
Chicago is a thriving metropolis that is attracting all kinds of Fortune 100 companies (and tens of thousands of their employees), with an incredibly diversified corporate base (transportation, tech, financial services, real estate/construction, insurance, tourism, aerospace, food), social/cultural offerings (museums, architecture, entertainment) that you have to go 2000 miles west or 1000 east to even remotely compare and are supported by a group of VERY OLD OLD money families (Crown, Pritzker) that have made the city their base.
Ppl that think Chicago is broke, don't know shyt.
Chicago has its issues because of the way it spends its money, NOT because it doesn't have money. There is a HUGE difference.