Samuel Insull purchased the land in 1924 with plans to develop it for residential use and create an English-style town.

The town's suburban development was stimulated by its being the western terminal of Chicago's Garfield Park rapid transit line.

These have provided residents with car-based travel in the region, however they also serve as barriers against access to neighboring communities.

Residential and retail development has consumed nearly all open land within the village, save for the protected 85-acre (340,000 m2) of Wolf Road Prairie.

[14] Westchester has a Walk Score of 43, meaning most errands require driving a car.

[15] The village also has several zoning provisions that foster car dependency, such as minimum parking requirements.

Westchester is completely within Illinois' 7th congressional district being represented by Danny Davis.

Constructed in 1986 and renovated in 1996, the complex consists of five 10-story towers encompassing more than 1 million square feet (93,000 m2) of office space.

Westbrook Corporate Center has won the 2000/2001 BOMA- International Office Building of the Year Award, 2000/2001 BOMA- North Central Region Office Building of the Year Award, and 1998/1999, 1999/2000, 2000/2001 BOMA- Suburban Chicago Office Building of the Year Award.

[31] The Chicago Tribune stated there was a decline in students in the area surrounding the school site.

Zoned students attend Proviso West High School in Hillside.

[27] Westchester residents may apply to Proviso Math & Science Academy in Forest Park.

Additionally, Westchester is home to Eden Lanes Bowling Alley, Focus Time Escape Rooms, the Wolf Road Prairie, the Westchester Woods Sledding Hill, 4 youth sports organizations, and multiple forest preserves.