A. G. Becker Property

The Harold Florsheim House is a historic house at 650 Sheridan Road in Highland Park, Illinois. The house was built in 1925–28 for businessman Harold M. Florsheim, who later became the president of Florsheim Shoes. Chicago architect Ernest Grunsfeld, who went on to design the Adler Planetarium, designed the house in the French Chateau style. The house includes a gable above the entrance, a multi-story three-sided bay window, casement windows, and a hip roof broken by dormers. Landscape architect Jens Jensen designed the house's grounds, making use of a ravine on the property to instill a sense of privacy.The house was added to the National Register of Historic Places on September 29, 1982.

Rosewood Park is a historic park on Roger Williams Avenue in Highland Park, Illinois. The park is the former site of the Julius Rosenwald Estate, which was built circa 1910 for businessman Julius Rosenwald. Landscape architect Jens Jensen designed the estate's grounds, which he also used as a studio; these became the modern park after the home's removal. The park includes a beach on Lake Michigan, the North Shore Sanitary District Tower (closed), an empty stone pool and artificial stream, and a walking path that leads to a bridge over a ravine. Jensen also planted wildflowers in the park, which still bloom annually in spring.The park was added to the National Register of Historic Places on September 29, 1982.

The John Taylor Snite House is an architecturally-significant house in Highland Park, Illinois, United States. It was built for John Taylor Snite, a prominent businessman and sailor.

Braeside School is a historic school at 124 Pierce Road in Highland Park, Illinois. Built in 1928, the Prairie School style school was designed by architect John S. Van Bergen. Van Bergen had worked for Frank Lloyd Wright and mainly designed Prairie School houses, including his own Highland Park home. His plan for the school focused on creating a home-like setting for students, which included large classrooms, natural lighting, and fireplaces. The school has a low, horizontally oriented shape with a hip roof, a characteristic Prairie School form.The school was added to the National Register of Historic Places on September 29, 1982.

The North Shore Sanitary District Tower is located in Rosewood Park, Highland Park, Illinois. It was built in 1931 to provide ventilation for the local sewer system. The brick tower is 50 feet (15 m) tall and topped by a spire. The tower features Art Deco elements, including the spire and its stone door trim and windowsills; the application of a formal architectural style is unusual in a purely functional building. It was added to the National Register of Historic Places on June 30, 1983.The tower is featured on the cover of the album Oceania by The Smashing Pumpkins.

The Lichtstern House is a historic house at 105 S. Deere Park Drive in Highland Park, Illinois. The house was built in 1919 for a businessman named E. Lichtstern. Arthur Heun, a Chicago architect known for designing homes for the upper class, designed the house. Heun's design primarily used Italian Villa architecture, which was inspired by Lichtstern's travels to Italy, but also includes some Prairie School elements. Its overall form, use of segmental arches, and balconies are typical of the Italian Villa style, but its leaded glass windows and overhanging eaves are Prairie School features.The house was added to the National Register of Historic Places on September 29, 1982.

The Mrs. Frank Geyso Houses are two neighboring houses at 450 and 456 Woodland Road in Highland Park, Illinois. The earlier house at 450 Woodland was built in 1923–25, while the later house was built in 1930. John S. Van Bergen, a prominent Chicago architect who designed several other homes in Highland Park, designed both houses in the Prairie School style. The house at 450 Woodland is a cottage-style building with a stucco exterior and wood detail work. The house at 456 Woodland is a brick building with an entrance pavilion, a balcony, and overhanging eaves.The houses were added to the National Register of Historic Places on September 29, 1982.

Ravinia Festival is an outdoor music venue in Highland Park, Illinois. It hosts a series of outdoor concerts and performances every summer from June to September. The first orchestra to perform at Ravinia Festival was the New York Philharmonic under Walter Damrosch on June 17, 1905, with the Chicago Tribune praising its "musical entertainment so satisfying in quality and so delightful in environment." It has been the summer home of the Chicago Symphony Orchestra (CSO) since 1936. Located in the Ravinia neighborhood, the venue operates on the grounds of the 36-acre (15 ha) Ravinia Park, with a variety of outdoor and indoor performing arts facilities, including the architectural prairie style Martin Theater. The Ravinia Festival attracts about 600,000 listeners to some 120 to 150 events that span all genres from classical music to jazz to music theater over each three-month summer season.The Ravinia neighborhood, once an incorporated village before annexation in 1899, is actively maintained by the Ravinia Neighbors Association, who work to enhance and preserve Ravinia's architecture, history, and environment. The business district on Roger Williams Ave., within walking distance from the Ravinia Festival grounds, includes neighborhood service businesses and restaurants. Ravinia takes its name from the numerous steep-sided ravines that slice the land.

Ravinia Park is a seasonal station on Metra's Union Pacific North Line located in Highland Park, Illinois. The station serves the Ravinia Festival, and trains only stop at the Ravinia Park station during concert season. Ravinia Park is 20.9 miles (33.6 km) away from Ogilvie Transportation Center, the southern terminus of the Union Pacific North Line. In Metra's zone-based fare system, Ravinia Park is located in zone E. (Metra honors dated concert e-tickets as a train fare to Ravinia on concert days.) Ravinia Park has two side platforms which serve two tracks. Ravinia Park is the only seasonal station in the Metra system. As of 2022, during the summer, Ravinia Park is served by seven inbound trains and eight outbound trains on weekdays, by four inbound trains and eight outbound trains on Saturdays, and by four inbound trains and seven outbound trains on Sundays. (Extra train RAV1 is excluded from this tally.) Trains with a "" note on the timetable will wait longer at the station for passengers to load and unload. During events on weekends, an extra outbound train RAV-1 departs Ogilvie Transportation Center, makes all stops to Evanston Central Street, then runs express to Ravinia Park, where it terminates at 6:25 P.M. An inbound train returns to Chicago after the event ends. The Ravinia Park station was temporarily closed in 2020 due to the cancellation of all concerts for the Ravinia Festival in 2020 in response to the ongoing COVID-19 pandemic. Service to Ravinia Park resumed in the summer of 2021.

The George Pick House is a historic house at 970 Sheridan Road in Highland Park, Illinois. The house was built in the early twentieth century for businessman George Pick. Prolific Chicago architect Howard Van Doren Shaw, who also designed several other homes in Highland Park, designed the house. Shaw gave the house an Eclectic Revival design with extensive detail work inspired by architectural styles from throughout Europe. The house's features include carved limestone birds, gables with decorative bargeboards, and an arcade at the entrance.The house was added to the National Register of Historic Places on September 29, 1982.

Braeside is a railroad station in Highland Park, Illinois serving Metra's Union Pacific North Line, in the Braeside neighborhood of Highland Park. It is located at 10 North St. Johns Avenue, just off Lake Cook Road. In Metra's zone-based fare schedule, Braeside is located in Zone E. As of 2018, Braeside is the 117th busiest of Metra's 236 non-downtown stations, with an average of 410 weekday boardings. Cook County Forest Preserves' Turnbull Woods and William N. Erickson Preserve are adjacent to the station, and the Chicago Botanic Garden is a mile away. Braeside Station has a warming hut on the inbound side of the track. The station is named after a nearby school. The station consists of two platforms and a waiting room/warming hut, but does not contain a ticket agent booth or restroom facilities. Northbound trains stop on the west platform and southbound trains stop on the east platform. Trains go south to Chicago’s Ogilvie Transportation Center, and as far north as Kenosha, Wisconsin. As of 2022, Braeside is served by 23 inbound trains and 21 outbound trains on weekdays, by 11 trains in each direction on Saturdays, and by eight trains in each direction on Sundays.

The Jens Jensen Summer House and Studio at 930-950 Dean Ave. in Highland Park, Illinois is associated with landscape architect Jens Jensen. It was listed on the National Register of Historic Places in 1991.