The only things your allowed to spear down there are rough fish- like carp. If you come up to Wisconsin you can tag panfish as well- which are actually good to eat.
I know of one or two other freedivers in the chicago area and a few scattered around Southern Wisconsin. Your best bet is to make it up to Freedive-A-Palooza next month to meet everyone. You can do a search on this site for more details, and a write up from last year's event, but it's going to be the weekend of July 23+24 in LAke Wazee.
I play unerwater hockey in MAdsion, and there's a club in the Milwaukee area, but Chicago has a really good team that practices 3-4 days a week. I think they would be your best bet to get into the water.
There's another freediver I just met who lives in the Lake Geneva area but only has Tuesdays off.
As far as lakes go Lake Michigan is the clearest one around. There are some lakes close to my house which are fun in the winter and early spring, but right now they are so thick with weeds that you could almost golf on them. Lake Michigan runs 40'-70' of vis this time of year, depending upon the winds and currents and the surface water can get pretty warm the end of the summer. I think that I just saw the NOAA bouy read 69(F) degrees surface temp in the Chicago area today!
I'm suppossed to be going out on the Lake to do a little salvage work tomorrow so I can let you know a little more about dive conditions then- if the weather holds.
Jon