Winnetka has often been called the "crown jewel" of Chicago's North Shore suburbs.
Much of Winnetka's charm derives from its varied terrain, the size, variety and tastefulness of its architecture, its one-of-a-kind shops, restaurants and services, and the nearly 3 miles of shoreline, with both public and private beaches along Lake Michigan.
What's most distinctive about Winnetka, however, is the richness of its civic traditions, the quality of its public and private schools, and the intensity with which its citizens maintain and enhance its character.
City services, park district
The Winnetka Park District offers a rich array of parks, beaches and other recreational facilities, including a public golf course, an ice arena, boating facilities, and the renowned A.C. Nielsen Tennis Center.
Since 1915 Winnetka has been governed through a non-partisan Caucus in which "everyone who has a vote has a voice."
Single-family homes account for nearly 90 percent of Winnetka's housing stock, over 90 percent of which is owner-occupied. There are several hundred condominium and townhome units in Winnetka, most in smaller in-fill complexes. A good selection of homes and condos are generally available for rental.
Over half of Winnetka's housing stock pre-dates World War II. In East Winnetka, nearly all of the homes are of pre-war vintage.
South of Elm St in East Winnetka the streets follow a classic north – south / east – west grid. North of Elm the streets depart from the grid and follow the rolling contours of the land.
Many grand estates are hidden from view east of Sheridan Rd, on sizable (by North Shore standards) parcels that drift down toward Lake Michigan.
Winnetka has a large number and variety of homes priced upwards of $3 million, but also has a number of older homes priced well under $1 million. A 1 bedroom condo in an older building carries a mid-$100s price tag, and 2 bedrooms can be found as low as the low $200s in converted buildings.
The teardown phenomenon is a major presence in Winnetka, with nearly ten percent of its homes having been demolished and replaced with architecturally contextual new homes.
Metra's Union Pacific North Line makes three stops in Winnetka and reaches downtown Chicago in 35 to 40 minutes. Pace bus routes provide access to points north and south. Taxis and limo services are readily available. Winnetka is the only North Shore suburb through which the Metra trains run below grade.
Shopping, dining, nightlife
Nightlife in Winnetka is home-centered or focused around the village's many civic, social, recreational, educational and charitable organizations.
Winnetkans also enjoy easy access to nearby upscale malls, including Old Orchard, Northbrook Court and the Spanish-style Plaza del Lago. On any given Saturday morning Winnetkans will encounter a throng of neighbors at a nearby Costco.
The K-4 Crow Island elementary school is listed on the National Register of Historic Places. Designed by Larry Perkins and Eero Saarinen, it opened in 1940 and has been acclaimed as one of the most architecturally significant schools in America.