I now live in Chicago, which is the third largest school district in the United States. It's completely broken.
* The schools are massively segregated -- both by income and by race. The wealthy leadership of the city clearly decided a long time ago to give up on the public school system and send their children to private school. Even in middle class neighborhoods like Hyde Park, the divide is clear: if you're poor or black, you go to the local public school. If you can afford it, you don't.
* The school district is trying to close down 50 odd elementary schools, almost all of them in the ghettos. Why? Because population loss has eroded the tax income from those areas to the point where they can barely operate anymore.
* The entire teachers union went on strike for a few days earlier this year to protest salary and benefit cuts, increased testing, and the city's neglect for the school system. They didn't really win -- the salary cuts were mostly averted, but the tests keep rolling in.
* For every 100 students who enters CPS as a freshman in high school, only 6 ever get a bachelors degree.
The schools back home in Minnesota aren't perfect or even particularly good. They're mediocre. They're ok. But they're so much better than in Chicago (and many other parts of the country) that I will seriously consider moving back to Minneapolis when I start having kids.