Chicago and Baltimore.
Check the statistics.
I’m going with Chicago as well.
Overrun with unionistas and corrupt politicians.
Chicago has a wide and varied economy which would preclude this sort of thing.
Baltimore was a prosperous, thriving city before it was taken over and controlled by a Marxist regime. Now it is fit for nothing less than an ash pit. Any city that celebrates poverty and thuggery is destined for oblivion.
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.