The Potawatomi people lived in the area until the 1833 Treaty of Chicago. Given the dry nature of most towns between Evanston and Kenosha, Highwood enjoyed a high per capita number of bars and taverns. 
Highwood was the location of the headquarters of the Chicago North Shore and Milwaukee Railroad, a defunct railroad whose North Shore Line ran parallel to the Chicago and North Western Railway's trackage now know today as Metra's Union Pacific/North line. This defunct railroad once carried over 28 million passengers in a single year during World War Two.
According to the 2010 census, the city has a total area of 0.71 square miles (1.8 km2), all land.
Oak Terrace Elementary School (K through 5); part of the North Shore School District 112.
Saint James School (pre-K through 8); Catholic.
As of the census of 2000, there were 4,143 people, 1,555 households, and 933 families residing in the city. The population density was 6,552.1 people per square mile (2,539.1/km²). There were 1,604 housing units at an average density of 2,536.7 per square mile (983.0/km²). The racial makeup of the city was 43.14% White, 2.15% African American, 0.58% Native American, 2.12% Asian, 0.05% Pacific Islander, 17.19% from other races, and 4.78% from two or more races. Hispanic or Latino of any race were 38.23% of the population.
There were 1,555 households out of which 29.8% had children under the age of 18 living with them, 43.2% were married couples living together, 10.0% had a female householder with no husband present, and 40.0% were non-families. 34.1% of all households were made up of individuals and 13.0% had someone living alone who was 65 years of age or older. The average household size was 2.60 and the average family size was 3.31.
In the city the population was spread out with 23.3% under the age of 18, 10.6% from 18 to 24, 33.8% from 25 to 44, 16.6% from 45 to 64, and 15.7% who were 65 years of age or older. The median age was 34 years. For every 100 females there were 99.1 males. For every 100 females age 18 and over, there were 98.0 males.
The median income for a household in the city was $42,993, and the median income for a family was $53,000. Males had a median income of $30,560 versus $27,560 for females. The per capita income for the city was $24,138. These income statistics are significantly lower than in surrounding towns. About 4.3% of families and 7.0% of the population were below the poverty line, including 9.9% of those under age 18 and 5.2% of those age 65 or over.
- "Geographic Identifiers: 2010 Demographic Profile Data (G001): Highwood city, Illinois". U.S. Census Bureau, American Factfinder. Retrieved December 7, 2012.
- "US Gazetteer files: 2010, 2000, and 1990". United States Census Bureau. 2011-02-12. Retrieved 2011-04-23.
- Encyclopedia of Chicago: Highwood http://www.encyclopedia.chicagohistory.org/pages/582.html Accessed November 29, 2013
- "2010 Census U.S. Gazetteer Files for Places – Illinois". United States Census. Retrieved 2012-10-13.
- "American FactFinder". United States Census Bureau. Retrieved 2008-01-31.