I'm reviving an old thread I know, but I've been enjoying a lot of early Chicago house again recently.
It kind of depends which artists sounds you're being inspired by.
Is is a more Mr Fingers / Virgo Four "deep" sound or the more acid side of things?
Virgo Four speak in interviews of using the Roland Alpha Juno and TR-505. Lots of the early Trax records releases feature the Roland TR-707 on drum duties. Of course there are lots of uses of the TB-303 on the acid side of things and of the TR-909 (but less than the 707 or Casio RZ-1 imho).
if I was going to try to get the early Chicago sound I would get something like the following, depending on availability and budget.
Drums = Roland TR-707 / Casio RZ-1 / TR-909 / TR-505 (could add 727, 808 or 626). Alternatively get a TR-8 an R-8.
Bass = Roland SH-101 / SH-2 / SH-9.
Pads/Chords = Roland Alpha Juno / Juno 106, 60 or 6 (or Ensoniq ESQ-1, Korg Polysix, Akai AX-60 or similar)
Sampler = Ensoniq Mirage / Akai S-950 / Ensoniq EPS-16 / Akai S-612 / Korg DSS-1.
At the moment I would choose 707, 101 and Juno 106 just for the pure fun aspect of those machines, trigger the 101 sequencer from the 707 trig out and probably sequence the 106 from one of the Roland MC-? midi sequencers or an Alesis MMT-8 then Record it to tape, preferably Tascam or Teac 4-track

any Yamaha DX or TX would be good for the FM "clonk" duties