"Windy City Rehab" follows real estate developer Alison Victoria as she renovates historic homes in Chicago. With the help of her contractor, Donovan Eckhardt, Alison takes on challenging projects to restore these old properties to their former glory. However, they face obstacles such as budget constraints, strict city regulations, and unexpected issues that arise during the renovation process. Despite the challenges, Alison is determined to revitalize these homes and turn a profit. The show highlights the beauty of Chicago's architecture and the dedication it takes to preserve its history.