Like much of the south side of Chicago, West Englewood was swampy grassland until it was settled by European immigrants in the 1840s. Farmers, mainly from Sweden and Germany, cleared and harvested the area, growing crops and maintaining a rural lifestyle. That was the norm until a commuter railroad line was built that cut through the region. The property near the tracks became more heavily developed and people started to take an interest in the budding section of town. Within decades, farms were subdivided and a residential district emerged.

Additional railroads were built that crisscrossed the neighborhood, which inspired the original name of the heavily-traveled locale: Junction Grove. (The neighborhood’s name was later changed to Englewood, named after the town in New Jersey.) Railroad workers that were employed to lay track and operate the trains eventually settled in and around Junction Grove, creating a viable railroad town.

The greater Englewood area (which included West Englewood, too) was annexed by Chicago in 1889, while construction was underway on the World’s Fair—also called the Columbian Exposition—in nearby Hyde Park. The event attracted more than 25 million visitors to the vicinity (which was a pretty impressive assemblage in the 1890s), effectively putting the south side of Chicago on the map. Just as had happened a few decades prior with the construction of the railroads, many of the workmen that were employed to help build the more than 200 temporary buildings for the fair grounds decided to stay in the area and erected homes in the neighboring Woodlawn and Englewood communities. Soon after the Exposition was held, electric streetcars were built to accommodate the growing population of Englewood, connecting the neighborhood to the rest of the city. Sidewalks and other basic amenities were incorporated into the region’s infrastructure in the following decade, and by 1907, a rapid transit elevated line (now the Green Line) was extended to the eastern boundary of West Englewood.

Thousands of Italian immigrants moved to Englewood during the interwar period, taking manufacturing jobs and working in the stockyards, which were located just to the north of West Englewood. In addition, Englewood was home to the garages where the city streetcars and busses were housed and serviced, so many area residents took up employment there as well. After an elevated train station opened at 63rd Street and Ashland Avenue, Ashland emerged as the primary commercial district in the neighborhood. The stretch between 63rd and 75th streets was soon lined with small storefronts, restaurants and taverns, creating a thriving business center for southwest side residents.

In the 1930s, the African American population of Englewood increased dramatically, as thousands poured into Chicago and other northern cities from the southern states. The trend would only increase over the next two decades, marking a major demographic shift in the neighborhood that had once been composed almost exclusively of German and Swedish immigrants. By 1950, African Americans made up nearly half of the residents in Englewood, and by 1980, the neighborhood was almost entirely populated by African American families. Other changes took place during that time as well, chiefly the rise of poverty in the region. When the stockyards closed down in the 1970s, many West Englewooders lost their jobs causing a number of residents—both black and white—to leave the area in search of work elsewhere.

Today, many of those trends have been reversed and there are many promising signs for the community. Improvements to local infrastructure have helped to increase property values, and many abandoned buildings have been demolished to clear the way for future development. Even after the neighborhood lost the bulk of its employment opportunities, West Englewood bounced back and is seeing rejuvenated real estate prices thanks to its proximity to Midway International Airport and the Dan Ryan Expressway. Parks are plentiful, the shopping district along Western Avenue has rebounded and homebuyers are once again eager to call West Englewood home.