Edward H. Bennett House and Studio

The Deer Path Inn is a historic hotel, originally named Deerpath Inn because of its previous location on Deerpath Road, is now located at 255 E. Illinois Road in Lake Forest, Illinois.

The Vine–Oakwood–Green Bay Road Historic District is a residential historic district in Lake Forest, Illinois. The district contains twenty houses on Oakwood Ave., Vine Ave., and Green Bay Road.

Market Square is a 103,000-square-foot (9,600 m2) neighborhood shopping center in Lake Forest, Illinois, United States, in the Chicago metropolitan area. Opened in 1916, it is often cited as the first planned shopping center in the United States, with common design and management and designated area for parking automobiles.Although Country Club Plaza (1923) in Kansas City, Missouri is generally credited as the first suburban and the first regional shopping center designed to accommodate shoppers arriving by automobile, Market Square was first with these features, but was neither suburban nor of "regional" size (400,000 sq. ft. or larger). Market Square was built within an already defined central retail district, replacing prior development. Lake Forest resident Arthur T. Aldis championed the notion of replacing the dilapidated business district of the town, and engaged architect Howard Van Doren Shaw.In Illinois, the first major center to be developed after Market Square was Spanish Court (1928). In celebration of the 2018 Illinois Bicentennial, Lake Forest Market Square was selected as one of the Illinois 200 Great Places by the American Institute of Architects Illinois component (AIA Illinois).

The West Park Neighborhood Historic District is a residential historic district surrounding West Park in Lake Forest, Illinois. The district includes 149 contributing buildings, most of which were built between 1907 and 1930, and West Park. Originally known as the Green Bay Addition, the neighborhood was planned in 1907 as the equivalent of a company town for the service workers at Lake Forest's many estates. Lake Forest was a popular home for the Chicago area's most wealthy residents in the early twentieth century, who typically built large estates that required teams of support workers to maintain. Architect Howard Van Doren Shaw, who also designed many of the estates, planned the neighborhood. While Shaw intended for the development to mainly use Tudor Revival architecture, few houses were designed in the style; the Colonial Revival, Folk Victorian, Craftsman, and American Foursquare styles were more common.The district was added to the National Register of Historic Places on November 14, 2012.

Lake Forest is a railroad station in Lake Forest, Illinois, served by Metra's Union Pacific North Line. The station, located at 691 North Western Avenue, is 28.3 miles (45.5 km) away from Ogilvie Transportation Center, the inbound terminus of the Union Pacific North Line, and also serves commuters who travel north to Kenosha, Wisconsin. In Metra's zone-based fare system, Lake Forest is in zone F. As of 2018, Lake Forest is the 70th busiest of Metra's 236 non-downtown stations, with an average of 747 weekday boardings. Lake Forest station is located in downtown Lake Forest and is in close proximity to the Lake Forest Library. The station has a ticket office which is open during the morning rush hour, Monday through Friday. As of April 25, 2022, Lake Forest is served by 46 trains (23 in each direction) on weekdays, by all 26 trains (13 in each direction) on Saturdays, and by all 18 trains (nine in each direction) on Sundays and holidays. This station is sometimes referred to as East Lake Forest, to avoid confusion with the Lake Forest station on the Milwaukee District North Line. Parking is available along the east side of the tracks along McKinley Road between Woodland Road and north of Illinois Road, along the east side of the tracks along Western Avenue between Illinois Road and Vine Avenue, and at numerous lots near the station. As with many suburban Metra stations, Pace buses serve commuters at the station. No connection between this station and the Lake Forest station on the Milwaukee District North Line is available, however. The current building was built in 1900 by the Chicago and North Western Railway to a design by architects Frost & Granger.

The Noble Judah Estate is a historic estate at 111 and 211 West Westminster Street in Lake Forest, Illinois, United States. The estate was built from 1925 to 1928 for lawyer Noble Brandon Judah, his wife and National Cash Register heiress Dorothy Patterson, and their children. It includes a main house, a garden, a pool, and several small outbuildings. The main house and the outbuildings were given French Renaissance Revival designs by architect Philip Lippincott Goodwin; their designs include steep roofs, decorative brickwork, and half-timbering. The estate's landscape design was inspired by traditional French gardens and includes a small Korean boxwood garden with a geometric layout.The estate was added to the National Register of Historic Places on August 3, 1990.

The 1906 U.S. Open was the twelfth U.S. Open, held June 28–29 at Onwentsia Club in Lake Forest, Illinois, a suburb north of Chicago. Alex Smith won the first of his two U.S. Open titles, seven strokes ahead of runner-up Willie Smith, his younger brother and the 1899 champion.Willie Anderson, three-time defending champion and club pro at Onwentsia, was the heavy favorite. He trailed Alex Smith by two strokes after the first 36 holes on Thursday, and by three after the third round on Friday morning, but an 84 that afternoon dropped him to a distant fifth. Smith posted rounds of 73-74-73-75 for 295, a U.S. Open record and the first sub-300 winning score. Not only did his brother Willie finish in second, his brother-in-law James Maiden tied for third.Smith's win marked the end of a streak where Scottish-born players won seven consecutive major championships. For the first time, no player from the inaugural U.S. Open in 1895 participated. Horace Rawlins, the first champion, had played in every edition until this year.

Onwentsia Club is an 18-hole golf course in the central United States, located in Lake Forest, Illinois, a suburb north of Chicago.

The Green Bay Road Historic District is a residential historic district in Lake Forest, Illinois. Centered on Green Bay Road, a historic postal and military road that once connected Chicago with Green Bay, Wisconsin, the district includes 147 contributing buildings. The houses in the district are mainly country estates built in the late nineteenth and early twentieth century for some of the Chicago area's wealthiest residents. The Onwentsia Club, a country club to which most of the district's residents belonged, was the center of the area's social life and is also part of the district. The district includes works by several prominent Chicago architects, including Howard Van Doren Shaw, David Adler, Ambrose Coghill Cramer, and Chester Howe Walcott. While the Arts and Crafts style preferred by Shaw is common in the district, most of the other houses are designed in revival styles, including Classical Revival, Renaissance Revival, Colonial Revival, and Tudor Revival.The district was added to the National Register of Historic Places on November 7, 1995.

Ragdale is the former summer retreat of Chicago architect Howard Van Doren Shaw (1869–1926), located in Lake Forest, Illinois. It is also the home of the Ragdale Foundation, an artist residency program that hosts creators from a number of disciplines: nonfiction and fiction writers, composers, poets, play- and screenwriters, visual artists, choreographers, as well as those from interdisciplinary interests.

Lake Forest High School, or LFHS, is a public four-year high school located in Lake Forest, Illinois, a North Shore suburb of Chicago, Illinois, in the United States. It is the only school of Lake Forest Community High School District 115, which serves the communities of Lake Forest, Lake Bluff, Knollwood, and smaller parts of Mettawa and North Chicago. It is fed by Lake Bluff Middle School, Lake Forest Country Day School, Saint Mary's, and Deer Path Middle School.

Lake Forest Country Day School (LFCDS), founded in 1888, is a coeducational, independent preK-8 school located on a 29-acre campus in Lake Forest, Illinois, USA, a suburb approximately 30 miles north of Chicago. The School serves families from more than 34 communities. The School is affiliated with the Country Day School movement and is a member of The National Association of Independent Schools, The Independent Schools Association of the Central States, The Lake Michigan Association of Independent Schools and The Secondary School Admission Testing Board. The school has a House System. The system does not, however, have any disciplinary aims or purpose. The houses are named after the school's four most prominent founders. They are the Alcott House, whose house color is purple, the Bell House, whose color is yellow, the Farwell house, whose color is blue, and the Mason house, whose color is red. The system is to bring a cross-grade feeling of unity throughout the school. The students all have buddies, all of which have a fairly wide age difference.