Calumet City (commonly referred to locally as "Cal City") was founded in 1893 when the villages of Schrumville and Sobieski Park merged under the name of West Hammond, since it lies on the west side of the Illinois-Indiana line from Hammond, Indiana.

[7] Bootleggers including Al Capone built on this basis once the Prohibition era arrived, and West Hammond gained the nickname of "Sin City".

[7][3] Frank LaPorte is believed to have been the member of the Chicago Outfit who was most responsible for developing and maintaining the "Sin Strip" area of Calumet City.

[9] In 1959, the state of Illinois conducted a police raid that resulted in 98 arrests and the seizure of business records.

[10] An article published in Chicago Daily News on June 2, 1959, exposed LaPorte as being instrumental in the illegal activities in Calumet City.

A landmark and point of pride among Cal City residents is the pair of large water towers painted like the popular "Have a Nice Day" smiley faces which are located on Ring Road near River Oaks Mall, the other State Street near Interstate 94.

John Belushi's "Joliet Jake" and Dan Aykroyd's "Elwood" characters from The Blues Brothers were born in Calumet City, and so is the orphanage they grew up in, which they save "on a mission from God" by paying $5,000 in property taxes from a $10,000 record deal at their concert, as well as "Ray's Music Exchange" that holds the famed Ray Charles "Shake Your Tail-Feather" scene of the movie.

In the book and film The Silence of the Lambs, Buffalo Bill is thought to be hiding in Calumet City, when he is actually in Belvedere, Ohio.

A photograph of the "Dolton" smiley water tower is featured on the back of the Dead Kennedys album Plastic Surgery Disasters.

In the Nine Inch Nails music video on the director's cut of the same film, the Smiley Tower and Dolton Avenue/State Street is featured.

They later named one of thoroughbred horse racing's most famed and successful enterprises, Calumet Farm, after the company.

In 2004, Alan Keyes purchased a raised ranch house in Calumet City to establish residency in Illinois so he could run for the U.S. Senate in place of Jack Ryan against Barack Obama, although instead of residing in the house, he officially moved into an apartment elsewhere in town, on Garfield Avenue.