Highwood is a city in Moraine Township, Lake County, Illinois, United States, located between Chicago and Kenosha. As of the 2010 census, the population was 5,405, and in 2018 the population was estimated to be 5,272. The city is just south of the Fort Sheridan Forest Preserve and is part of the group of communities known as the North Shore. It is known for its entertainment, restaurants, and bars. According to the Guinness World Records it has the most bars per mile.
Highwood is located in southeastern Lake County at 42°12′19″N 87°48′44″W, on a ridge 100 feet (30 m) above the elevation of Lake Michigan.
According to the 2010 census, Highwood has a total area of 0.71 square miles (1.84 km2), all land.
Originally, the land was owned by the Potawatomi until the 1833 when it was ceded to the United States through the Treaty of Chicago. The first non-Native American settled in the town in 1846. In 1851 Highwood became the headquarter location of the Chicago North Shore and Milwaukee Railroad, which ran parallel to the Chicago and North Western Railway's and is now know today as Metra's Union Pacific/North line. Thomas Curley suggested the name High Woods because the land was the highest ground between Chicago and Milwaukee and was covered with trees.
In 1886 civil and labor unrest in Chicago eventually led to the Haymarket Riot.