Home to the nationally acclaimed New Trier High School, Winnetka is a classic North Shore town located 19 miles north of downtown Chicago. Elegant homes and grand estates line beautifully landscaped streets. Housing styles include English, French Provincial, New England, Colonial and Tudor. Celebrated onscreen in movies like “Ferris Bueller’s Day Off,” “Sixteen Candles,” and the “Home Alone” series, Winnetka is also the boyhood home of former U.S. Secretary of Defense Donald Rumsfeld and the birthplace of late actor Rock Hudson.

Winnetka residents attend one of three elementary schools and two middle schools in the Winnetka Public Schools System District 36. The curriculum of these schools is based on The Winnetka Plan, an educational philosophy developed by former superintendent Carleton Washburne. The plan, which stressed creative activities and emotional and social development, is still followed today. Winnetka is located in New Trier Township and students attend New Trier High School for grades 9 through 12. Parochial schools are available as an alternative to public education. The private North Shore Country Day School, the Hadley School for the Blind, and the Music Center of the North Shore are also in the village. Oakton Community College serves Winnetka residents.

Incorporated in 1869, and Native American for “beautiful land”, Winnetka is a very wealthy village bordered by Kenilworth to the south, Northfield to the west, Glencoe to the north, and Lake Michigan to the east. The village consists of peaceful tree-lined streets and family-centered neighborhoods, as well as four small business districts or downtown areas maintained by the Winnetka Chamber of Commerce. The districts, located along Green Bay Road, consist of restaurants, shops, and small businesses. Whether residents want to eat outside at O’Neil’s on a crisp, fall evening, grab a steaming hot beverage at Caribou Coffee during the frozen winter, or shop for clothes at E Street Denim, Winnetka’s downtown has something for everyone. Wilmette’s Edens Plaza Shopping Center is located nearby and has many fine stores. Westfield Old Orchard in Skokie features a variety of department stores including Bloomingdales, Nordstroms, Lord & Taylor and Macy's.

Winnetka offers a variety of recreational facilities and activities. The Winnetka Park District provides residents with a large choice of programs including sports, camps, classes, performing arts, and waterfront activities. A Native American term for “beautiful land”, Winnetka has no shortage of stunning parks, green space, and beaches. The Skokie Lagoons make up part of the Forest Preserve area along Forestway Drive and are perfect for residents who love biking, fishing, boating, and bird watching. Winnetka also features an indoor tennis club, a public golf course, an ice rink, and a boat launch at Lloyd Beach. The Winnetka Community House is a non-profit organization that offers even more activities and programs and also acts as a meeting place for clubs and organizations. In addition, Winnetka and its surrounding communities offer a multitude of country clubs for residents to choose from. Ten country clubs can be found in the surrounding area.

Evanston Hospital is a level I trauma center with a medical staff of over 700. Highland Park Hospital, to the north, is a level II trauma center with a staff of over 400. Evanston Hospital is a teaching facility incorporated with Northwestern University Medical School. Highland Park serves as a training and resource center for paramedics.

Winnetka’s public transportation system allows residents quick and easy access to the city. Winnetka has three Metra stations located at Elm Street, Indian Hill, and Hubbard Woods. There are numerous Pace bus stops throughout the village and the Linden stop of the Purple Line “L” train, located in Wilmette, is just minutes south. Using Sheridan Road to Lake Shore Drive or the Edens Expressway (I-94), Winnetka is about a 20 to 30 minute drive to the city.