They take a drive through the mostly black and affluent Pill Hill neighborhood on the far south side of Chicago. It can roughly be bounded by Jeffery, 87th Street, Stony Island and the 91st Street. It was said to be the neighborhood of former County Board President John Stroger while he was still healthy.
You know check out this post I made just about two years ago, the primary setting of this book that I mentioned takes place in Pill Hill.
PS: You know I just realized that they have a couple of other videos of other places on the south side. I will share them with you over the next few days.