Nestled along the shore of Lake Michigan, Winnetka is located in the New Trier Township within Cook County. Ivy-draped estates, quaint shops, and cozy restaurants cluster the tree-lined streets of this North Shore hamlet. Along the lake, a series of beaches, boat launches, parks, and athletic fields add to the area’s ambiance. Winnetka boasts a tranquil environment, paired with an unmatched pleasant atmosphere and a sense of elegance. The community continues to be mentioned atop as one of the North Shore’s favorite places to call home. Click here for more. Winnetka is located approximately 16 miles north of downtown Chicago, along the shores of Lake Michigan. Winnetka commuters can catch Metra’s Union Pacific North Line at Elm Street, Indian Hill or Hubbard Woods station. The area is also served by Pace bus and conveniently located nearby the Edens Expressway (I-94) for drivers. Winnetka has 23 community parks, three swimming beaches, a boating beach, a dog beach, an 18-hole public golf course and an outdoor ice rink.