The typical asking rate per listing is in the $10's per square foot per year. The Southwest Side submarket is seeing a an increase in rates. In the last 3 months, the median rate increased $19 per sqft per year.
Compared to the rest of the Chicagoland market, the Southwest Side submarket has less expensive rates, so you should have no trouble finding a great deal in this discounted submarket.
In the last 90 days, 9 listings have been made available, which means office spaces are probably going fast. You'll want to be prepared to tour spaces as quick as possible. About 11% of the listings in the Southwest Side are subleases, so you might be able to find a shorter term or below market rent. There aren't many listings below 2,000 square feet available, so finding a space for a small business might be tough.
The standard measurement for office space in this area is around 1,500 sqft. Most properties in this area are close to 1 stories. Most buildings in this market were built in 1954 and are Class A.