The finances of the city will inevitably end in some combination of bankruptcy and ruin thanks to toxic pensions, the abuse of them, and the city's refusal to prudently manage around them (though in fairness the pensions have been so toxic that no prudence could keep up with them). It's just algebra. The city (and state) is already insolvent and just resorts to various can-kicking tactics.
Violent crime is tolerated and ignored by most. No one dare point out the elephant in the room that it's committed wildly disproportionately by minorities. A white kid trolls the Cubs with that bogus "okay" symbol and the city goes berserk; 25 black kids shot over the weekend and it's a collective shrug. Things tend to settle at the level of expectations, and a liberal ethos has set expectations for the black community to be all but nonexistent.
The suburbs are dying, and this is reflected in real estate values. Follow the Chicago Tribune's architecture columnist, Dennis Rodkin, on Twitter. Every day this guy features a new home sale in the suburbs where it's sold for less than what it sold for 20, even 30 years ago. It's depressing to see how Illinois' failed policies have a massive tax against families' greatest asset.
The city is dying, as population loss continues at a rapid pace. Chicago has lost more millionaires than any other city in the world over the last decade. The stats are all readily available with a quick search. The real estate values will inevitably follow the path of the suburbs.
The new governor - a bored billionaire heir who's never accomplished anything on his own merit in his life - is about to effectively double the state income tax. The death spiral accelerates. When you tax something you get less of it.
The corruption of the city politicians is tolerated and even joked about as The Chicago Way. Corruption has been normalized, just like it has for places like Russia. These sorts of cultural rot are difficult to reverse.
Death spiral.