There are often differences when you choose to find condos for rent in Chicago as opposed to either a professionally managed building or an owner who owns an entire 2-3 story building. Since with condo rentals you are dealing with an owner who typically only owns the one apartment in the entire building and the unit may have been purchased as an investment, you may often find a condo for rent in somewhat better shape than a standard rental. However, obviously every owner is different in how much they invest or tend to their property.
Condos for rent can be found in all size apartments and in just about all neighborhoods. If you want to be close to Downtown Chicago, you can often find condo rentals in neighborhoods such as the South Loop, West Loop, Gold Coast, River North and Streeterville. If you want to be in a slightly more affordable yet popular area, condos for rent are available in areas like Lincoln Park, Lakeview and Logan Square. Some of the most bang for your buck in the condo rental market is in Chicago's northern most areas Rogers Park and Edgewater as well as the northwest side of the city where you can get gut rehabbed apartments at an reasonable price.
One downside to renting a condo in Chicago is that most of these buildings (especially the condo hi rise buildings) have condo boards that review the applications to rent and they often charge condo fees (normally ranging from $200-$600) to move in/out and to process the application. This is separate from a security deposit or any fees the actual property owner may charge. There also normally is a set of written condo rules and regulations that each new tenant has to sign and agree to which may have a few tighter guidelines than most other rental buildings.