On average, listings lease in the $10's per square foot per year. The Southwest Side region is experiencing a decline in rates. In the last 3 months, the median rate fell $3 per sqft per year. That's a 17% decline in rent.
Compared to the rest of the Chicagoland market, the Southwest Side region has less expensive rates, so you should have no trouble finding a great deal in this discounted submarket.
In the last 90 days, 6 listings have come on the market, which means leases most likley are going fast. You'll want to be prepared to tour spaces as quick as possible. About 17% of the listings in the Southwest Side are subleases, so you might be able to sign a shorter term by taking over a previous lease. There aren't many listings below 2,000 square feet on the market, so finding a space for a small business might be tough.
The standard measurement for office space in this area is around 2,200 sqft. Most buildings in this area are close to 1 stories. Most buildings in this market were built in 1952 and are Class A.