Winnetka is a village located approximately 14 miles (23 km) north of downtown Chicago in Cook County, Illinois.
The first houses were built in 1836. That year Erastus Patterson and his family arrived from Vermont and opened a tavern to service passengers on the Green Bay Trail post road. The village was first subdivided in 1854 by Charles Peck and Walter S. Gurnee, President of Chicago, Milwaukee & St. Paul Railroad. Winnetka's first school opened in 1856. The town was incorporated in 1869 with a population of 450.
The oldest surviving house in Winnetka is the Schmidt-Burnham House. It was relocated in the 2003 from its previous location on Tower Road to the Crow Island Woods.[3]
Winnetka’s neighborhoods include estates and homes designed by distinguished architects including George Washington Maher, Walter Burley Griffin, John S. Van Bergen, Robert Seyfarth, Howard Van Doren Shaw, and David Adler.
The Chicago and Milwaukee Railway was built in 1855 through Winnetka, connecting its namesake cities, this eventually became the Chicago and North Western Transportation Company. In 1995 the C&NW was merged into the Union Pacific. Only Metra trains are operated on this track now, freight operations ended in the late 1980s.

The Chicago, North Shore and Milwaukee electric interurban was built through Winnetka and the North Shore in the first decade of the 1900s and the line through Winnetka was removed in 1955. This is now the Green Bay Trail bicycle path.
During the Great Depression both the C&NW and the C&NSM lines were rebuilt into a grade separated right of way mostly below street level to prevent crossing accidents.
The Crow Island School, designed by Eero Saarinen, was declared a National Historical Landmark in 1990. It was declared 12th among all buildings and the best architectural design of all schools. 10,000 people showed up for the opening in 1938.