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Winnetka is a station on Metra's Union Pacific North Line located in Winnetka, Illinois. Winnetka station, located at 754 Elm Street in Winnetka, is 16.6 miles (26.7 km) away from Ogilvie Transportation Center, the inbound terminus of the Union Pacific North Line. In Metra's zone-based fare structure, Winnetka is in zone D. As of 2018, Winnetka is the 68th busiest of Metra's 236 non-downtown stations, with an average of 754 weekday boardings.Winnetka station is located in a below-grade trench. The platforms are accessible via stairs from Elm and Oak Streets and a passenger bridge. An elevator for handicapped access is also located on the passenger bridge. The station consists of two side platforms which serve two tracks. A station house is located at street level; the station house is open from 5:15 A.M. to 1:15 P.M., and tickets are sold on weekdays. Parking is available in a lot adjacent to the station house. The Green Bay Trail, a hiking and bicycle trail, runs east of and parallel to the railroad tracks at Winnetka and can be accessed from the inbound platform. As of April 25, 2022, Winnetka is served by all 35 trains in each direction on weekdays, by all 13 trains in each direction on Saturdays, and by all nine trains in each direction on Sundays. On weekdays, seven outbound trains terminate at Winnetka, and six inbound trains originate from this station. Winnetka was originally built at grade level when it served the Chicago and North Western Railway. As an increasing amount of railroad traffic came through Winnetka, the railroad crossings became unsafe, and 29 people had been killed at railroad crossings by 1937 despite safety efforts by the city and the railroad. After the deaths of two prominent Winnetka women at the Pine Street crossing on October 20, 1937, Winnetkans demanded that the grade crossings be removed. The city elected to put the tracks in a below-grade trench to avoid dividing the city with an elevated railroad. With the help of funding from the Public Works Administration, the tracks were lowered into a trench by 1943. Winnetka and Hubbard Woods stations were located at street level with access to station platforms by stairs from a pedestrian walkway across the tracks, and Indian Hill became an elevated station.

The Community House, also known as the Winnetka Community House, is a 3-acre (1.2 ha) community center located at 620 Lincoln Avenue in Winnetka, Illinois. The center was completed in 1911, though it has been expanded several times since. Architect Arthur Coffin designed the building primarily in the Tudor Revival style, though his design also incorporated elements of the Prairie School. The building hosted a wide variety of community activities for all ages and genders, including sports and gym classes in its gymnasium, music and photography groups, billiards, and lectures; by the end of 1911, 51 different groups had begun meeting in the center. While the Community House was nonsectarian, its establishment and operation were heavily influenced by Winnetka's Congregational Church and inspired by its principles of community, education, and youth outreach. In keeping with the popular contemporary settlement movement, the church also planned the center as a settlement house; while it lacked living spaces, it included other typical settlement houses features such as its gymnasium, dining areas, and meeting rooms.The community center was listed on the National Register of Historic Places on August 30, 2007.

The Dr. Paul W. and Eunice Greeley House is a historic residence in Winnetka, Illinois. Dr. Greeley was a major figure in the field of plastic surgery around World War II and later served as department chair at two universities. Designed by Frank Polito, and with a dining room probably designed by Fiske Kimball, the Classical Revival residence closely follows a Greek Revival design and was listed on the National Register of Historic Places in 2011.

The Lola Maverick Lloyd House is a historic house at 455 Birch Street in Winnetka, Illinois. The house was built in 1920 for pacifist and feminist activist Lola Maverick Lloyd and her four children. At the time, Lloyd had recently undergone a public divorce from William Bross Lloyd; while she expressed a desire to move back to Texas, where she had grown up, her custody agreement required her to stay in Illinois. Architect Charles Haag designed the house with the assistance of Lloyd herself; their design is in the Arts and Crafts style and includes influences from both Texas and Haag's native Sweden. The house has a distinctive red, cream, turquoise and teal color scheme and features carved wooden decorations inspired by animals and nature, gable ends with board-and-batten siding, and shed-roofed dormers projecting from the roof. While she often rented it while traveling to Europe to advance her activist work, Lloyd considered the house her home until her death in 1944, and it remained in her family for the rest of the twentieth century.The house was added to the National Register of Historic Places on February 1, 2006.

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.

Winnetka () is a village in Cook County, Illinois, United States, located 16 miles (26 km) north of downtown Chicago. The population was 12,316 as of 2019. The village is one of the wealthiest places in the nation in terms of household income. It was the second-ranked Illinois community on Bloomberg's 2019 Richest Places Annual Index. In 2020, 24/7 Wall St ranked Winnetka as the second-best small town to live in the United States.

The Wayside, also known as the Henry Demarest Lloyd House, is a historic house at 830 Sheridan Road in Winnetka, Illinois, United States. An extensively altered mid-19th century country inn, it was from 1880 until his death in 1903 the principal residence of Henry Demarest Lloyd (1847–1903). Lloyd was a leading "muckraking" journalist of the late 19th century, and a major editorial voice against corporate monopolies and for organized labor. His house was declared a National Historic Landmark in 1966.

Edgecliff (aka the Max Epstein House) is a Samuel Abraham Marx–designed estate in Winnetka, Illinois, in the wealthiest region of Chicago's affluent North Shore suburbs. It is notable for once having the highest residential property taxes in Cook County, Illinois.

Indian Hill is a railroad station in the southernmost portion of Winnetka, Illinois, an affluent suburb north of Chicago. One of three stations serving that village, the Indian Hill stop is served by Metra's Union Pacific North Line trains, with service to Ogilvie Transportation Center in downtown Chicago. Northbound trains go as far as Kenosha, Wisconsin. In Metra's zone-based fare schedule, Indian Hill is in zone D. As of 2018, Indian Hill is the 125th busiest of Metra's 236 non-downtown stations, with an average of 387 weekday boardings.The station is located on Winnetka's southern border, at Green Bay Road and Winnetka Avenue, less than a mile west of Lake Michigan. Outbound trains stop on the west platform, and inbound trains stop on the east platform. Indian Hill lacks a ticket agent office, passengers boarding must buy their tickets on board the train. Travel time to Ogilvie ranges from 31 minutes to 39 minutes, depending on the train. As of April 25, 2022, Indian Hill is served by 26 inbound trains and 25 outbound trains on weekdays, by 11 trains in each direction on Saturdays, and by eight trains in each direction on Sundays. Indian Hill is at the southern end of what is known as "The Big Ditch", which carries the railroad under Winnetka. Before the early 1940s, Winnetka had grade crossings, where accidents caused 31 deaths between 1912 and 1937. The village, federal government and railroad authorities funded a five-year project to rebuild the railroad below grade, and this was completed in 1943, after which there were no more level crossings in Winnetka.

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.

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 Louis B. Kuppenheimer Jr. House is a historic house at 789 Burr Avenue in Winnetka, Illinois. The house was built in 1937-38 for Louis B. Kuppenheimer Jr. and his family; Kuppenheimer had inherited a large manor house from his father, who had been the president of a clothing company, but wished to move to a smaller home. Architect David Adler, a prominent architect best known for designing country houses, designed the house in the French Renaissance Revival style. The house's design includes a recessed arched entrance, French doors along the south and west sides, a service wing with a mansard roof, a porch wing, and a dentillated cornice. While the house is smaller than most of Adler's works, it still exhibits the typical themes of his designs, such as eclecticism, symmetry, and attention to detail.The house was added to the National Register of Historic Places on December 4, 2017.