the southside and south suburbs reminds me of detroit. working class, lots of strip malls, some ethnic enclaves. majority black.
hyde park is nice. bronzeville has some nice areas to it. i know people who live in south shore who like it.
pilsen is the southside but its gentrfying very quickly. becoming more like the north side east of ashland. west to western is developing but is still very mexican. little village is all mexican. but now youre getting more into whether youre in the "west" or "south."
traditionally (at least in the last 30-40 years since the great influx of mexican immigrants) the south side is black, the north side is white, and the west side is mexican. that's a way too general way to look at it, but there's some truth to it.
a lot of the southside is not very nice. back of the yards, etc.
the west side is worse in a lot of places.
but the northside is my favorite place in the whole country. one of the greatest parts of the greatest city in america.