Waukegan began as an Potawatomi Indian settlement until a French trading post was established by Pere Marquette around 1673. It was first called Little Fort but was changed by proud residents who wanted to change the description of "little" in the city name to Waukegan, a Potawatomi word for "fort." Early settlers were initially attracted to Waukegan as a port city and shipped produce and grain from Lake and McHenry County farms to Chicago. The creation of the Illinois Parallel Railroad (now the Union Pacific Railroad) in 1855 stimulated interest in Waukegan as a manufacturing center. The town continued to grow and diversify, and Waukegan was incorporated as a city on February 23, 1859, with an area of 5.62 square miles. Today the city has a population of approximately 92,066 (2006), which makes it the ninth largest city in the state of Illinois.
Waukegan citizens value the community they live in and support many community enrichment programs. One of these is the the Waukegan Park Service that, through its Cultural Arts Division and the Jack Benny Center for the Arts, offers fine arts and cultural arts programs. Also supported is the Bowen Heritage Circle/Haines Museum, Schornick Theatre, and the Visual Arts Center. Arts programming includes special events, dance, music, theatre, and visual arts, as well as a professional theatre and opera company, a community symphony orchestra and a concert chorus. Programs allow students, lecturers, artists, musicians, and actors opportunities to contribute to the culturally diverse community. The park district works cooperatively with the historical society’s volunteer board by providing a museum, a museum supervisor, and a research library. Historically significant archives, events, tours, programs, and exhibits provide opportunities to learn about the community and its history. The people of Waukegan present several special events and festivals annually; they include the Oakwood Cemetery Walk, the Dandelion Wine and Fine Arts Festival and Green Town - Through the Eyes of the Artist.
Waukegan is considered the hometown of comedian Jack Benny and celebrates his memory with the fine arts program and a Waukegan middle school named for him. There is also a statue of him that stands in the downtown. Waukegan is the birthplace of writer Ray Bradbury (born 1920), whose great-grandfather was mayor of the city in 1882. The Waukegan of the 1920s appears as "Green Town" in several of Bradbury's fictional works, particularly Dandelion Wine. Ray Bradbury Park, named in the author's honor, includes the bridge over the ravine featured in that novel.