I’d add two points to riverandsasha3’s posts. First, I’d include the West Side to what’s been said about the South Side. Schools on the West Side are badly under-resourced, too. Many things seem to work that way in Chicago, not just education. The North Side generally gets better services than the South Side and the West Side.
Second, while the West Side is mostly black and Latino and on the whole very poor, the South Side is more mixed both racially and socioeconomically… There are some black middle class areas, and are some predominantly white neighborhoods, at least if you define the South Side broadly to include the predominantly white Southwest Side. I get the impression that public schools on the Southwest Side aren’t all that great, either, but then, I’m not sure how many white kids attend those schools. Many seem to be in Catholic schools which are a mixed bag in terms of educational quality… That seems to be part and parcel of the de facto racial segregation that is still predominant in Chicago, on the South Side in a more extreme form than on the North Side, though the North Side isn’t great, either. I lived in Chicago for 10 years—on the North Side, I might add—and I mostly loved it, but the politics and sociology of race in Chicago are abominable.