There can be no answer to this question. First of all Chicago is 30 miles long and 10 miles wide. Condos are in 2 flats and in 900 unit buildings and everything in between. Old, new, updated and rehabbed. Small and huge. It is just too open a question. Even if you can you narrow it down the next questions are is it a foreclosure, short sale or regular sale? Can the property be rented... so many more questions. I think if you are looking to buy the real questions are quite different.