With its large yards, single-family homes and un-grid-like blocks, the far Northwest Side neighborhood of Wildwood more resembles a suburban subdivision than a part of Chicago’s urban cityscape. This out-of-the-way residential hamlet is about 12 miles from the Loop and is considered part of the larger Forest Glen community. It is bordered to the west by the Caldwell Woods Forest Preserve, which draws outdoor enthusiasts with its acres of untouched woodlands, wide open green spaces and access to the North Branch Trail (a treasure among Chicago’s hikers and bikers).

Long before Wildwood became the tree-lined neighborhood it is today, it was home to Native American tribes. The area was plush with wild game and the nearby Chicago River provided a great source of fresh water. In 1828, the land that included Wildwood and the Caldwell Forest Preserve was given by the United States to a half-Irish Potawatomi chief named Billy Caldwell for orchestrating several territorial treaties between the U.S. government and the Potawatomi Indians. Later on, Chief Caldwell parceled off the land and sold it to farmers and settlers. It was annexed to the city of Chicago in 1889 and has remained a fairly remote enclave of residences to this day.   

There is a small section of commercial development at the southernmost tip of Wildwood, where the Edgebrook Metra station is located. This area has a few restaurants and shops along Devon and Caldwell avenues. Downtown commuters can pick up the Metra Union Pacific North train here or take Caldwell Avenue or Touhy Avenue to the Edens Expressway (I-94), which is just east of the neighborhood. Even though Wildwood is pretty far removed from the city center, its proximity to major transportation arteries keeps residents connected with all the cultural aspects of living in Chicago.

Properties in Wildwood are surrounded by towering oaks and maples that shade backyard decks and patios and provide a sense of permanence. Green grass lawns stretch from one lot to the next, defined by leafy hedges and privacy fences. Unlike most Chicago neighborhoods, the houses in Wildwood have ample space between them—much like you’d find in a small town. In some parts of the community street-entrance driveways with attached garages are the norm while other areas maintain the city’s traditional alley-entrance setup with a detached garage behind the home. A variety of architecture adorns Wildwood’s wide residential roads. Many houses are two stories and range from stately Georgians to time-honored Colonials. There is also a showing of modest brick ranches and frame homes here. But no matter what your address, you’ll appreciate the serene backdrop and tranquil vibe of this beautiful North Side Chicago neighborhood.