The original inhabitants of the swampy prairie that is now Englewood were Mascouten Indians. In 1840 the United States Government Land Office in Chicago officially documented the land that is now Englewood as habitable and early settlers started to claim sections of the territory for building their homesteads. A nearby ridge became a well-used path by Native Americans and settlers alike, and over time the path grew into what is today Vincennes Avenue. One of the earliest residents reported looking south from what is now 66th Street and seeing nothing but wetlands for miles—a far cry from the multitude of houses and businesses that now occupy the terrain.

In the 1850s, railroad tracks were built that cut through Englewood, turning it into a major railroad hub known as the Chicago Junction. In the following years, the population of Englewood grew rapidly, and it was given a big shot in the arm as a result of the Chicago Fire. As the city was rebuilding, residents were forced to seek housing in more remote regions, and Englewood was one of the more attractive destinations because of its easy accessibility via train.

A few years after the fire, developers began laying out the foundation for a viable self-sufficient community between Wentworth Avenue and Halsted Street from 55th Street to 71st Street (present-day Englewood). Soon an increasing number of Swedish, German and Irish railroad workers, attracted by employment opportunities, started moving to the area from other nearby neighborhoods such as Bridgeport and Back-of-the-Yards.

By 1905 Englewood Station had become a crucial junction and passenger depot for three railroads: the Chicago, Rock Island and Pacific Railroad, the New York Central Railroad, and the Pennsylvania Railroad. It was perhaps most famous for the glamorous eastbound streamliner trains such as the 20th Century Limited and the Broadway Limited, which were synonymous with style, speed and grace, and provided the most luxurious means of traveling between Chicago and New York City. At its peak as a station in 1928, more than 1,000 passengers a day traveled through Englewood.

In the roaring 1920s, Englewood’s shopping district at Halsted and 63rd streets was the city’s second busiest shopping district, only topped by the Loop. By the end of the decade, Sears had established a $1.5 million department store there. Sadly, the ensuing stock market crash had a severe impact on the prosperity of the high-flying neighborhood, and in many ways it never recovered.

The ensuing years after World War II saw increasing stratification, as many of Englewood’s Irish, Swedish and German residents headed to other neighborhoods. The 'Great Migration' of African Americans from the South brought a surge of new black residents to the area, and by 1950 the population of the neighborhood was about 10 percent African American. Many more families moved to Englewood in the late-1950s when large construction projects such as the Dan Ryan Expressway displaced thousands of residents on the south side.

During the 1960s, in an attempt to inject the neighborhood with a commercial revitalization, Chicago officials commissioned the building of a pedestrian mall in Englewood at Halsted and 63rd streets. In the end, the attempt was a failed one, and critics of the project claimed that rather than creating more business, it actually precipitated a decline in small retail stores that had been in the neighborhood for years. Many of those small stores did return, but it was too late. In the 1980s the shopping center struggled as it lost almost all of its anchor stores—Wieboldt’s, Sears and others closed their doors or relocated elsewhere. The mall became a hodgepodge of smaller specialty shops that sell wigs, clothing, shoes, groceries and the like.

The pedestrian mall—much like the State Street mall in the Loop—was abandoned as a failed idea in the late 1980s, and Halsted Street was once again opened to traffic at 63rd Street. In 1999, Mayor Richard M. Daley announced a $256 million revitalization plan for Englewood, which included a new police station, housing, and the relocation of Kennedy-King College from 6800 Wentworth Avenue to a 40-acre site at 63rd and Halsted streets, in the heart of Englewood. With the ensuing changes initiated by Kennedy-King’s emergence on the scene, the neighborhood now has some renewed interest in its real estate. What many had long considered a blighted community has recently become an area with a strong base for future growth.