Blood Money - Gangland (easiliy his best release), Choppa Talk and Drug Wars are not as consistent, but there are dope tracks.
Bo Deal is slept on, almost every release is good. Try his latest one - Out Wit A Bang, if you like it check for some earlier music.
SD - Life of a Savage series, 3rd i don't like that much but still some good cuts. his album Truly Blessed is also good, some soft songs, some hard songs.
King Louie - Drilluminati series, TONY.
Fredo Santana - Fredo Kruger, It's a Scary Site, Trappin ain't dead (first half of the album is great, later tracks suffer from some bad mixing or shyt, noises on background)
Percy Jones - Montreal to Chiraq. he is not from Chicago, but a lot of drillers on feat, some songs are dope as fukk
Gino Marley - Raised In The Streets.
Bosstop - At Yo Neck.
Tray Savage - Brain Dead.
Montana of 300 has good tracks, but his release is woat, can't recommend.