Back in the day, we're talking hundreds of years ago, much of the terrain south of Chicago was marshy swampland that was difficult to harvest or develop. But people are innovative and with the help of technological advances, the sections of the soggy earth were eventually transformed into useful soil—for laying railroad tracks that is.

West Elsdon was originally populated by European immigrants (mostly Irish and Germans) who moved to the area to work on the railroads that were being constructed in the region. As a result of population growth and a mounting need for increased infrastructure, the community was annexed into Chicago along with much of the rest of the southwest side in 1889. The main employer in the area at the time was the Grand Trunk Railroad, which connected Chicago to the northeastern United States and Canada. But even with the neighborhood's recent incorporation into the larger city of Chicago and a thriving rail transportation industry, much of the region still remained submerged in swampy water.

With significant breakthroughs in drainage technology (hey, if the Dutch could do it, why couldn't we, right?) West Elsdon and the surrounding vicinity were effectively drained in the 1920s. Still, the neighborhood didn't really take-off (so to speak) until the Chicago Municipal Airport (present-day Midway Airport) was opened in 1927 directly to the west of West Elsdon.

In many ways, the strength and prosperity of the neighborhood has always been largely contingent on its position along major trade and travel routes. In the 1960s, to accommodate the increasing domestic air travel at Midway Airport, construction began on the Stevenson Expressway (I-55). When completed in the late 1960s, the Stevenson provided area residents with a convenient and speedy means of traveling to downtown Chicago for work or leisure. Then, in the early 1990s, the neighborhood received another boost with the opening of the elevated CTA Orange Line train, which has a stop in the neighborhood. The Orange Line is still the most recent expansion to the CTA rapid transit network, and as a result it's one of the fastest and smoothest rides in the city.

Over the years, the demographic makeup of West Elsdon has changed considerably from the time when it attracted a cultural mix of immigrant railroad workers. Many of the aging European populations have since moved on to the suburbs or to Chicago's north side and have been replaced by incoming Mexican immigrants and Mexican-American families. Today the West Elsdon neighborhood remains solidly working class, and is one of the most comfortable and family-friendly neighborhoods in the southwest side.
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