Throughout its history, Jefferson Park has been an important transportation hub for those headed into or out of Chicago. This, along with the fact that the area has been common entry point for new immigrants for over 100 years, has helped the neighborhood gain its reputation as being "the Gateway to Chicago." Farmers began to settle in the area in the 1830s, and the former Indian trails they used to travel to the city to sell their produce were soon turned into oft-traveled plank roads (now known as Milwaukee Avenue and Elston Avenue). These roads became such popular routes that "farmers traveling to and from the city often stopped to water their horses, pick up supplies, or rest" in the area, which was then called Jefferson Township. The population grew when railroads extended into the area in the late 1800s, and "by 1900, a web of street railway lines extended on Lawrence, Milwaukee, and Elston Avenues." With these new means of transportation came an influx of immigrants, the majority of them from Poland, Germany and other Eastern European countries.
"The development of Jefferson Park slowed through the mid-1950's because of a lack of modern transportation," but this soon changed when it was announced that the Northwest Expressway (now Kennedy Expressway) would be built, a portion of which would run through the neighborhood. The CTA constructed "a terminal in Jefferson Park that connected CTA and Regional Transit Authority bus routes, a Greyhound bus stop, a Chicago & North Western commuter railroad station, and an Elevated line," further solidifying the area's identity as a major transportation hub.