Chicago has been on the verge of fiscal collapse since the 1800s. Maybe it will happen tomorrow, who knows.
Articles like these aren't really about Chicago though; Chicago is just the convenient punching bag for the short period of time near an election when conservatives need to pretend to care about fiscal responsibility, and then go back to being every bit as irresponsible as any liberal could be.
https://news.ycombinator.com/item?id=40713116