Part of the Irving Park community area, the neighborhood now known as Old Irving began its initial period of growth in the 1870s soon after four men from New York purchased a large amount of farm land in the area. Their plans to continue farming the land quickly changed "after seeing the success of suburban communities which had recently opened for settlement," and they began to subdivide the land to create an exclusive suburb. Wealthy Chicagoans that wanted to escape the city moved into newly built mansions, and by the time the community was annexed into the city in 1889, "over 200 homes had been built in the original subdivision."
The neighborhood steadily gained population throughout the early 1900s, but "the prosperity following the war was diminished when it was learned the Northwest (Kennedy) Expressway would cut directly through the heart of" the community. This resulted in the loss of numerous historic homes and businesses, but at the same time also contributed to the area's rebirth in the 1980s. Along with being within close proximity to the Blue Line and the expressway, "a wider audience discovered the beautiful homes and rich history of the area," which again made Old Irving a popular place to live.