Located within the South Shore community, the Jackson Park Highlands is one of the South Side’s premier residential neighborhoods.

So named because a portion of it lay on a ridge above a lagoon, the Jackson Park Highlands came into being on August 3rd, 1905. The Highlands is an eighty-acre subdivision spearheaded by Chicago alderman, lawyer, and real estate entrepreneur, Frank Ira Bennett, as well as Charles Bour.

Of the two, Bennett is the most well-known, and Bennett Avenue within the Highlands is named after him. Born on a farm in Henry County, Illinois, near Galva, on October 17, 1858, Bennett was the son of a leading Illinois lawyer, John I. Bennett who served for many years as master of chancery in the United States courts. Educated at Hyde Park High School and the Union College of Law, he was admitted to the bar in 1880. He subsequently divided his career between the law, a real estate business, and public service, serving as assessor for the Town of Hyde Park in 1888, and was elected to the City Council in 1897 as alderman for the Seventh Ward.

His biography is included in A. N. Waterman's Historical Review of Chicago and Cook County, published in 1908, which noted that: "On the South Side Mr. Bennett has been a leader in promoting real estate activity and in laying out new subdivisions." The entry further noted that, having been brought up on a farm, Bennett retained a lifelong fondness for outdoor life and sports. While a lucrative financial reward was undoubtedly an incentive for Bennett to develop the Jackson Park Highlands, an additional appeal may have been the idea of resi­dential living in proximity to the rambling landscape of Jackson Park and the creation of a country-like residential area away from the center of the city.

More significant growth came during the building boom of the 1920s, when the Highlands was one of three model communities planned within Chicago. A minimum lot width of fifty feet was required, and houses had to be set back thirty feet from the front property line. Houses had to be faced with brick or stone and roofs covered with tile or slate. Alleys were eliminated, and all utilities were placed underground. Most of its earliest residents migrated from the then-elegant Washington Park neighborhood. From its inception to the present, its character as an enclave of gracious, commodious houses on ample, carefully landscaped lots has re­mained unchanged. The majority of the houses, built between 1905 and 1940, reflect the rich and diverse forms and fashions of American residential architecture for twentieth­ century single-family homes before World War II.

Source: Preliminary Staff Summary of Information on the Jackson Park Highlands District, Submitted to the Commission on Chicago Landmarks. October, 1988.