Strong Towns covers this: The whole “the suburbs are fine/better” is part of the pyramid scheme. Sure, they’re fine for the first 20-40 years. But then they deteriorate and the maintenance costs pile up. Tax rates increase to compensate. Wealthy residents who basically run their lives on tax avoidance simply move to a more recently developed suburb and the rest stay and suffer through a broke government, forced to do things like rely on police fines to sustain the budget (Ferguson, MO).

The “ring of wealth” moves around over the decades due to the pyramid scheme effect.

It isn’t hard to find suburbs with far worse roads and infrastructure than the city of Chicago. Maple Heights, OH, Parma, OH, Euclid, OH. I’m sure Chicagoland has plenty of them, I’m just not familiar with them. You also won’t see any upper middle class people living in these suburbs, not anymore.

Because Chicago is supporting the rest of the state. We have horrible return on investment on our tax dollars.

If Chicago seceded and formed a city-state the Chicago budget crisis would end overnight.

Depends on which suburbs you’re referring to. The north shore, full of old suburbs, has awful roads. Most of the side streets are un-maintained original cobblestone. It’s like driving on a wave pool.