The evolution of Chicago's Jefferson Park neighborhood began with the arrival of John Kinzie Clark. Known as the first white settler in Chicago, Clark also was one of the first pioneers of this northwest side neighborhood. In 1830, he arrived and constructed a log cabin hotel. The section of land where Clark built his inn was heavily traveled by merchants and traders journeying to and from Chicago. Subsequently, the Jefferson settlement became a convenient rest stop for these people and gained quickly gained popularity.

In 1850, the roads now known as Milwaukee Avenue and Elston Avenue were built to better connect people to Chicago. Jefferson Township, a separate entity from Chicago, was formed in that same year. A thriving village with several businesses emerged in the area where today Milwaukee Avenue and Higgins Road connect. Not long after, a rail line (Chicago & North Western) was extended and that, too, ran through this exact spot.

By 1889, Jefferson Township was annexed by Chicago. A system of streetcars was established along Lawrence, Milwaukee, and Elston avenues at the turn of the century. This furthered the accessibility of the area and many working class immigrants, mostly Polish and German, began to populate the area. But by the 1950s, what was once a major transportation hub fell increasingly still. With this slowdown in travel through the neighborhood, the population growth also dwindled.

Things started to turn around at the end of the decade; the Kennedy Expressway was constructed through the heart of Jefferson Park, offering residents a convenient passage in and out of the city. Ten years later, the CTA expanded Jefferson Park transportation by opening up a bus station, followed by a Greyhound station, and Blue Line train stop. The multiple means of transportation has helped the neighborhood return to its former glory as a central hub for the northwest side.

Today, remnants of the original residential architecture such as late 19th century Victorians still stand in the neighborhood, which is rapidly growing again with a new influx of families.