The most expensive homes in Illinois are all located in the Chicago-Naperville-Elgin metro area. Kenilworth tops the list with a typical home value of $1.92M, followed by Winnetka at $1.72M and Glencoe at $1.51M. Home values have generally increased over the past year and five years, with some cities seeing over 50% growth in five years. High mortgage rates and rising prices impact affordability statewide.