The price per square foot of asphalt in Chicago can vary depending on several factors, including the quality of the materials, the thickness of the asphalt layer, and the complexity of the project. On average, homeowners can expect to pay between $3 to $5 per square foot for basic asphalt paving. However, costs may increase if additional services such as grading, excavation, or removal of an existing driveway are required. It's best to request a detailed quote from a professional paving contractor to get an accurate estimate based on your specific needs.