Generally yes — but if you own multiple properties, there are portfolio options that can simplify and reduce your cost. Each rental property carries its own distinct liability exposure, location risk, and coverage needs, so a single blanket policy rarely fits well. However, landlords with two or more properties may qualify for a commercial landlord package that covers all properties under one policy with one renewal date. We help Chicago landlords evaluate whether individual policies or a portfolio approach makes more financial sense for their situation.