It won’t be Chicago. At least, not as far as bankruptcy goes. About a third of the entire US economy runs through that town and there’s plenty of blood left to suck. Now if we’re talking crime rate, urban depopulation, etc. then sure, Chicago has a bleak future.
Detroit was far more prosperous than Chicago in the 1960’s and 1970’s if you look at median income, home ownership, automobile ownership, etc.
It is crime, parasites and politicians that destroy a City.
The Daley machine, as corrupt as it was, kept Chicago from falling off the cliff into unstoppable crime and dysfunction. The Daley machine is no more. Chicago is doomed. The hard working, responsible and successful people are leaving. The thugs and parasites will remain.
The only question is how long will the State of Illinois and the Federal taxpayers continue to subsidize the crime and dysfunction in Chicago.