Its initial purpose was as a collection of model homes that would overlook the prized Jackson Park, which had hosted the World's Fair less than a decade prior.
The neighborhood featured (and is still present) some of the most innovative concepts of the time, including large front yard setbacks, 50-foot lot widths, underground utilities, and no alleys.
When Chicago annexed Hyde Park just in time for the 1890 census (to beat out Philadelphia as the second largest metro-area in the nation), the Highlands were left under governorship of the South Shore area.
At the time of World War II, the neighborhood saw huge loss in residence and a destruction of the area was suggested.
Notable residents have included members of the Whitehall Family, Jesse Jackson, Ramsey Lewis, Bo Diddley, Enrico Fermi and Gale Sayers.