The reply might depend on your specific situation, but, regardless of your location, there are a few factors that you might think about as you decide to invest in rental property. These include the following: the breadth of tenants' rights, required disclosures, any restrictions on deposits or pet rent, and how challenging an eviction may be if the tenancy doesn't work out. That said, as Illinois is the home of colleges and universities like the University of Chicago, Northwestern University, and the University of Illinois in addition to tourist attractions like Millenium Park, Willis Tower, and the Art Institute of Chicago, there should be no lack of short- or long-term tenants if the property is close to them.