Robert and Suzanne Drucker House

Regina Dominican is a college preparatory Catholic school for girls grades 9-12, located in Wilmette, Illinois.

Wilmette Public Schools District 39 (D39) is a school district headquartered in the Mikaelian Education Center in Wilmette, Illinois in the Chicago metropolitan area. The boundaries of the school district include most of Wilmette, a small part of southeastern Glenview, with a population of 27,247 as of 2019, and a neighborhood in unincorporated Cook County with Winnetka addresses.

New Trier Township () is one of 29 townships in Cook County, Illinois, United States. As of the 2010 census, its population was 55,424.The township contains New Trier High School, but the borders of the school district do not line up exactly with the borders of the township.

Loyola Academy is a private, Catholic, co-educational college preparatory high school run by the USA Midwest Province of the Society of Jesus in Wilmette, Illinois, a northern suburb of Chicago, and in the Roman Catholic Archdiocese of Chicago. It is a member of the Jesuit Secondary Education Association and the largest Jesuit high school in America, with over 2,000 students from more than 80 different zip codes throughout the Chicago area. It was founded by the Jesuits in 1909.

Crow Island School in Winnetka, Illinois, is an elementary school operated by Winnetka Public Schools. It significant for its progressive philosophy and its International Style architecture. The design of its building was a collaboration between the Chicago firm of Perkins, Wheeler and Will and Eliel and Eero Saarinen. It currently serves kindergarten through fourth grade students. The school was established in 1940-41. Sebastian Hinton's prototype "jungle gym" is located here, having been moved from Horace Mann School in 1940. The school was awarded the Twenty-five Year Award by the American Institute of Architects in 1971. It was declared a National Historic Landmark in 1990. In celebration of the 2018 Illinois Bicentennial, Crow Island School was selected as one of the Illinois 200 Great Places by the American Institute of Architects Illinois component (AIA Illinois).

The Anita Willets Burnham Log House, located at 1140 Willow Rd. in the Crow Island Woods of Winnetka, Illinois, United States, was the home and studio of artist and author Anita Willets-Burnham. The log house, which is 2+1⁄2 stories tall and made of hand-hewn, squared oak logs, was built approximately 1836 on a farmstead in south central Winnetka. In 1917, Willets-Burnham purchased the house and moved it to 1401 Tower Road in northwest Winnetka; she placed an addition on the home in the same year. Willets-Burnham was a prominent painter whose work was based on Impressionism and realism, and she often painted outdoors; in fact, she discovered the log house while on a painting expedition. She continued her artistic career until the 1930s, when she became a writer and authored Round the World on a Penny, an account of her travels in the 1920s. Willets-Burham lived in the cabin until her death in 1956.Willets-Burnham placed a great importance on preserving the house due to its age and place in early Winnetka settlement, and she furnished the house with period 1800s furniture rather than contemporary items. Her preservation efforts predate any other attempts to save North Shore log cabins by over fifty years, and the cabin is now the largest and likely the oldest surviving log cabin in the area. After her death, her two daughters lived in the home until their deaths in 1978 and 2000. The Winnetka Historical Society then inherited the home and relocated it to Crow Island Woods to save it from demolition. It was added to the National Register of Historic Places on June 2, 2005.

The James B. Irving House is a historic house at 2771 Crawford Avenue in Evanston, Illinois. The house was built in 1928 for James Irving and his family; it was originally located at 1318 Isabella Street in neighboring Wilmette. John S. Van Bergen, a prominent Chicago-area architect and former employee of Frank Lloyd Wright, designed the Prairie School house. The house has a stucco exterior with bands of ornamental wood, rows of casement windows, and a low hip roof with wide overhanging eaves, all characteristic features of the Prairie School. The interior has a split-level plan, allowing for separate floors while keeping the house low to the ground. To avoid its demolition, the house was moved from its Wilmette site to its current location in 2014–15.The house was added to the National Register of Historic Places on February 5, 2021.

No Man's Land, Illinois was never an official place name, but has been used to refer to at least two areas that fit the broader meaning of No man's land.

Wilmette is a village in New Trier Township, Cook County, Illinois, United States. Bordering Lake Michigan, it is located 14 miles (23 km) north of Chicago's downtown district (4 mi or 6 km from Chicago's northern border) and had a population at the 2010 census of 27,087. In 2020, Wilmette was ranked by Niche.com as the best place to raise a family in Cook County based on a variety of factors including public schools grade, percentage of residents with a bachelors degree or higher, crime & safety grade, family amenities, walkability grade, percentage of households with children, and access to parks and other recreational activities. Wilmette is also home to Central Elementary School and Romona Elementary School, both recent recipients of the National Blue Ribbon award bestowed by the U.S. Department of Education.

The Gross Point Village Hall, located at 609 Ridge Road in Wilmette, Illinois, was the village hall of the defunct village of Gross Point, Illinois. The village of Gross Point, named for a French description of a turn in nearby Lake Michigan's shoreline, was settled from the 1830s onward and incorporated in 1874. In 1896, Gross Point built a village hall to both house its government and serve as a community center. The two-story brick building has a Victorian design with two projecting front entrances, which originally led to the fire department and the village offices respectively. The small village relied heavily on alcohol taxes to fund its government, and had many taverns as a result; protests from prohibitionists in nearby Evanston, combined with opposition to new taxes to fund a sewer system, led to the village voting to dissolve itself in 1919. The village hall was sold to a private resident to pay back debts from the sewer system.The building was added to the National Register of Historic Places on August 5, 1991. It is now home to the Wilmette Historical Museum.

North Shore Country Day School is a selective prep school in Winnetka, Illinois. It took its current form as a coeducational school in 1919 during the Country Day School movement, though it started as the Rugby School for Boys (1893-1900) and Girton School for Girls (1900-1918). It consists of a lower school, a middle school, and an upper school. North Shore Country Day School offers a liberal arts education with students who represent the community values of respect and inclusiveness.

Indian Hill is an unincorporated community in New Trier Township, Cook County, Illinois south of Winnetka. The center of the community is located near Indian Hill station on Green Bay Road. It is home to a small "downtown" section, near the train station by the intersection of Winnetka Avenue. It takes its name from a nearby golf club, and has a population of about 6,000.