A traveler in the area in 1833 described visiting a village of bark-covered structures where he ate roasted corn with a chief named Nic-sa-mah at a site likely located south of present-day Clavey Road and east of the Edens Expressway.

In 1847, two German immigrants, John Hettinger and John Peterman founded a town along Lake Michigan, which they called St. John's. Soon, the town was abandoned, due to questions regarding ownership of the land. Three years later, another German Immigrant, Jacob Clinton Bloom, founded Port Clinton, which happened to be just south of St. John's. Port Clinton was described by Elijah Middlebrook Haines as "one of the most promising villages in the city". In 1854, a lighthouse was built in Port Clinton, thanks to funding by the US Congress and sponsorships from Illinois representatives. Despite having a functioning lighthouse with a keeper, a pier, sawmill, and a plank road, Port Clinton did not have a train station in 1855. In 1860, Port Clinton stopped growing as a town, and the lighthouse was shut down.

In 1867, ten men purchased Highland Park for $39,198.70. They were the original stockholders of the Highland Park Building Company. Following construction of the Chicago and Milwaukee Railroad, a depot was established at Highland Park and a plat, extending south to Central Avenue, was laid out in 1856. At that point, Highland Park was settled on mostly scattered farms and undeveloped forested land. Highland Park was established as a city on March 11, 1869, with a population of 500, and evolved from the two settlements of St. John and Port Clinton; St. John's Avenue and Port Clinton Square are named after the settlements. Highland Park was named from its parklike setting at a lofty elevation relative to the lake, and was given its name from Walter S. Gurnee. The town annexed the village of Ravinia in 1899.

Highland Park has several attractions including a downtown shopping district and the Ravinia Festival. Ravinia Festival is an open-air pavilion seating 3,200, which hosts classical, pop, jazz and Latin concerts in the summers. It has been the summer home of the Chicago Symphony Orchestra since 1936. Concert-goers can purchase seats in the covered pavilion or tickets to sit on the lawn. Many visitors arrive early and picnic on the lawn before and during concerts. The festival is located in Ravinia District, originally an artists' colony, which still retains much of its early character and architecture.

Highland Park has several landmark structures listed in the National Register of Historic Places, notably the Willits House by Frank Lloyd Wright. In addition to several houses designed by Wright, the National Register lists homes designed by prominent architects including John S. Van Bergen, Howard Van Doren Shaw, Robert E. Seyfarth, and David Adler. Landscape architect Jens Jensen lived in Highland Park and designed a number of projects in the community that are listed on the register.

There are three public beaches in Highland Park: Rosewood Beach, Moraine Beach (part of which is available for off-leash dogs), and Park Avenue Beach (which also has a boating facility). Highland Park is also home to the North Shore Yacht Club.