Yes, it seems very likely Chicago will be next. I grew up in Detroit, from 1950-1976. In 1973, 3 years after I started studying Rand and Mises, I predicted the bankruptcy (then got outta Dodge). Economics being a science, but not a predictive science in an exact sense, I only said: it may take years, but it will happen.
I don't see how Chicago, and then others under long-term Democratic rule, can avoid the same fate.
I don't see how Chicago, and then others under long-term Democratic rule, can avoid the same fate.