Once you factor in repairs and vacancy and any other hidden costs you will most likely be making little to nothing. I would say drop the attachment to the building because you lived there and find a place that has better numbers. In Chicago a huge factor is association fees, if you can find a building with lower association it will help your bottom line.
Also consider while Chicago is a good market in the US the housing market in the US is at probably an all time high.
Also consider while Chicago is a good market in the US the housing market in the US is at probably an all time high.