[pdovy]

Yeah as a transplant Chicagoan I'd have to disagree, on balance our infrastructure is pretty good. CTA works well enough for me to commute daily for the last 8 years without owning a car, and they've been systematically replacing water and gas lines around my neighborhood for the past few years. Not to mention new green / public space investments like the 606, Maggie Daley Park, etc.

Road resurfacing is pretty good where I am, but oddly is largely a function of how effective the alderman for your ward is, since a lot of the cost typically comes out of their budget.

The real problems with the city IMHO are massive unfunded pension liabilities and a huge segregation problem between the north/south sides.