"The Windy City" – The best-known nickname for Chicago.
"Second City" – Used in a 1950's New Yorker article by A. J. Liebling.
"Chitown" – Often used in slang in one song name "Convoy".
"Chicagoland" – Because of its surrounding suburbs.
"City of the Big Shoulders" – From Carl Sandburg's poem 1914.
"Hog Butcher for the World" – Poem from Carl Sandburg's.
"Beirut by the Lake" – From a Wall Street Journal article in 1980's.
"Chi-city" – Used by Kanye West in the song "Homecoming" and Common in the song "Chi-City"
"Chi-Congo" - Reference to the war-torn region of Africa's Congo.
"City by the Lake" – Used as early in 1890's.
"City in a Garden" – From Latin motto "Urbs in Horto"
"City of Bullets" - Referring to the incredible amount of gun violence that exists in the city proper.
"City on the Make" – From poem "Chicago, City on the Make" (1951)
"Great Commercial Tree" – From the State Anthem of Illinois
"Heart of America" – Location in the center of the United States.
"My Kind of Town" – From the song "My Kind of Town (Chicago Is)"
"Paris on the Prairie" – From the 1909 plan for the City of Chicago created by Daniel Burnham.
"Sweet Home" – From the Robert Johnson song Sweet Home Chicago.
"That Toddling Town" – According to the lyrics of the song "Chicago".
"The Big Onion" – In parallel with a popular New York nickname, "The Big Apple"
"The Black City" – a reference to the pre-1893 World's Fair Chicago which site was called "The White City".
"The Chi" – Short for the word 'Chicago'
"The Chill" – Also used by rap musicians.
"The City Beautiful" – A reference to the reform movement sparked by the World's Columbian Exposition.
"The City That Works" – According to former Mayor Richard J. Daley
"The Great State of Chicago" –A reference to the great political, cultural, social and ideological divide between the metropolis that is Chicago and the rest of the mostly agricultural State of Illinois.
"The Jewel of the Midwest" – Often used to describe Chicago and its various tourist destinations.
"The Third Coast" – As a reference to its long Lake Michigan shoreline.
"Chi-beria" – A play on Siberia, a nickname largely used during the 2014 North American Cold Wave.
"The Cogs" – A play on the second syllable of Chicago: 'cags.
"Chi-raq" – Due to intense gang activity and the perceived worsening of shooting incidents.