A friend of mine used to rent an Azteck out of Shaumburg for $130 wet a few months ago. His check out was only like 1.5 which isn't too bad. Might be worth taking a ride out there to see if they are still renting it for that price.
Luman Air out of Aurora had a Dutchess that I used to rent. Decent plane, but a little expensive for a Dutchess if you ask me. $165 wet plus the check out which was one flight about 2 hours if you had I think 500TT and 50 multi. Otherwise it was a 10 hour checkout. Ouch!
Cougar Aviation has a Grumman Cougar that they rent, but i'm not sure how much they charge or what the check out is like.
Illinois Aviation Academy (formerly Scott Aviation) out of DuPage has an Azteck (I think) that they rent. Again not sure on the price or checkout. Scott used to have a Seneca V that they charged some rediculous rate for... somewhere in the neighborhood of $300/hour. Not sure if it's still there though.
Clow had a C310 that they charged, I think, $210/hour wet. I can't remember what the checkout was though.
I'm not sure about singles, but I would check Illinois Aviation Academy. When it was Scott, I think they had some faster singles like a C182.