Maple Avenue/Maple Lane Historic District

Highland Park High School (HPHS) is a public four-year high school located in Highland Park, Illinois, a North Shore suburb of Chicago, Illinois, in the United States. It is part of Township High School District 113. From 1900 to 1904, the school was known as Deerfield High School. The high school served both Deerfield (renamed Moraine in 1998) and Shields townships from 1904 until 1936 and was Deerfield-Shields High School. The building of Lake Forest High School in 1936 provided a school to serve Shields Township students. This led to the return of the name Highland Park High School. A new, separate Deerfield High School opened 20 years later to serve the growing population.

Music Arts School was a community music school in Highland Park, Illinois from 1952 to 2007. It offered private lessons on guitar, bass guitar, piano, keyboard, Drums, world percussion, violin, viola, cello, saxophone, clarinet, flute, recorder, and voice. It also had a curriculum of group classes including programs for both adults and young children. Music Arts School began as a private music school in 1952. Pianist Mortimer Scheff founded the school and continued to head it until retiring in 2005. From 2001 to 2007, the school functioned as a non-profit. In September 2007, Music Arts School merged with the Music Institute of Chicago. Now known as the Highland Park Campus of MIC, the school continues to serve the North Shore of Chicago with individual music lessons and group music classes. In the years since becoming a non-profit organization, the school has grown upon its base of individual instruction by creating a curriculum of group music classes. Current subjects include Suzuki method, Adult Group Guitar, Musikgarten (early childhood music education), and Musicianship (music theory and history).

The Mr. Fred L. Mandel Jr. House is a French Eclectic house in Highland Park, Illinois. Designed by David Saul Klafter, the house was built for a Mandel Brothers executive.

The Humer Building is a historic commercial building at 1894 Sheridan Road in Highland Park, Illinois. Built in 1926, the building houses two retail spaces on its first floor and office space on its second floor. Architect John S. Van Bergen, a former employee of Frank Lloyd Wright, designed the Prairie School building. While Van Bergen designed many homes in the same style, it was not commonly used in commercial buildings, and the Humer Building's design is unique among commercial buildings in Chicago's northern suburbs. The building features ribbon windows, geometric designs on the inside, and patterned glass on its staircase, all typical Prairie School elements.The building was added to the National Register of Historic Places on September 29, 1982.

The Samuel Holmes House is a historic house at 2693 Sheridan Road in Highland Park, Illinois. Built in 1926, the Shingle style house was designed by architect Robert Seyfarth. The house is one of several Seyfarth-designed buildings in Highland Park and a rare example of the Shingle style in the city. The house's design includes an asymmetrical form, a gable roof with inset dormers, and a cedar shake sided exterior. Noted landscape architect Jens Jensen designed the house's grounds.The house was added to the National Register of Historic Places on September 29, 1982.

The Linden Park Place-Belle Avenue Historic District is a residential historic district in Highland Park, Illinois. The district includes 34 houses along Linden Park Place, Park Avenue, Linden Avenue, Elm Place, Park Lane, and Belle Avenue. The district includes the work of noteworthy architects such as George W. Maher and Robert Seyfarth. It also includes several homes built from pattern books during the first wave of Highland Park's development in the 1870s. Architectural styles present in the district include Victorian Gothic, Italianate, and Prairie School.The district was added to the National Register of Historic Places on December 13, 1983.

The Renaissance Place is one of the first "new urbanist" mixed-use developments of its kind located in the Chicago suburb of Highland Park, Illinois. It was designed in a vernacular style respectful of the history of this place. It includes several different buildings and styles of architecture appropriate for each use. The project opened in late 2007, and was home to the third Saks Fifth Avenue location in Illinois until it closed in December 2012. Even though it is a new development, occupancy is almost 100%. Above street-level retailers are condominiums, offices and a fine arts movie theater served by underground parking, grade level parking and street parking. The development has been featured in the 2005 Urban Land Institute Handbook on Mixed Use Development; the 2003 Urban Land Institute Handbook on Town Center Development; and the 2002 Urban Land Institute Handbook on Place Making: Developing Town Centers, Main Streets and Urban Villages. The facility was master planned and designed by the international architectural firm of Suttle Mindlin and has been a major factor in the revitalization of downtown Highland Park.

The Jean Butz James Museum is a historic house and former museum at 326 Central Avenue in Highland Park, Illinois. The Italianate house was built in 1871, two years after Highland Park's establishment. The Highland Park Building Company built the house without a buyer, as it expected that the new city would attract many affluent Chicagoans in the coming years. Its design includes a yellow brick exterior, bracketed eaves, and a widow's walk. The Highland Park Historical Society bought the house in 1969 and converted it to a historic house museum, which opened in 1972.The house was added to the National Register of Historic Places on September 29, 1982. The Highland Park Historical Society closed the museum and relocated in 2015.

The Evert House is a historic house at 2687 Logan Street in Highland Park, Illinois. The Highland Park Building Company built the house for Rev. W. W. Evert in 1872. The company, which built houses that buyers chose from pattern books, was responsible for many of Highland Park's early homes and community buildings. The house has a Second Empire design, a relatively uncommon style in the city. It features a mansard roof with two dormers and bracketed eaves.The house was added to the National Register of Historic Places on September 29, 1982.

On July 4, 2022, a mass shooting occurred during an Independence Day parade in Highland Park, Illinois, United States. The shooting occurred at 10:14 a.m. CDT (UTC−05:00), roughly 15 minutes after the parade had started. Seven people were killed, and forty-eight others were wounded by bullets or shrapnel. Authorities apprehended 21-year-old Robert Eugene Crimo III more than eight hours after the shooting and charged him the next day with seven counts of first-degree murder. On July 27, the charges were upgraded to 21 counts of first-degree murder, 48 counts of attempted murder, and 48 counts of aggravated battery.

The Highland Park Water Tower is a historic water tower on the west side of Green Bay Road in Highland Park, Illinois. Built in 1929–30, the brick water tower is 125 feet (38 m) tall, making it the tallest structure in Highland Park. The tower is Highland Park's third water tower and serves as a visual and symbolic landmark for the city. Its design features tall brick arches on its eight sides and a classical pediment above its entrance. The tower's water tank is capable of holding 500,000 U.S. gallons (1,900,000 L).The tower was added to the National Register of Historic Places on September 29, 1982.

The Highland Park Public Library is the public library serving Highland Park, Illinois. It is located at 494 Laurel Ave across the intersection from the Metra station.