Don't know how old your pops is, but Numero Group has put out a bunch of stuff that revolves around older eras of Chicago.
Light on the Southside is fukking excellent. It's a compilation of late 1970s R&B and Chicago blues. It comes with a large coffee table book of photographs of Southside club-goers in the late 1970s. Highly recommended.
They've also done extensive compilations for
Twinight Records (an Chicago soul record label, reissues of
Syl Johnson and a
compilation/DVD of a public access show that features post-disco and early rap from Chicago.