- Franklin Pierce Adams, columnist
- John Anderson, founder and publisher Skandinaven
- Nelson Algren, writer
- K. A. Applegate, author
- Saul Bellow, author; awarded Nobel Prize in Literature
- Allan Bloom, writer and translator
- Ray Bradbury, author
- Gwendolyn Brooks, poet
- Algis Budrys, author
- Edgar Rice Burroughs, writer
- Chris Bury, journalist
- Jack Cafferty, journalist
- Jack Canfield, author (Chicken Soup for The Soul)
- John Chancellor, journalist
- Raymond Chandler, writer
- Sandra Cisneros, author
- Daniel Cohen, children's writer
- Michael Crichton, writer
- James Gould Cozzens, novelist
- Philip K. Dick, writer
- Charles Dickinson, writer
- Mike Downey, newspaper columnist
- Finley Peter Dunne, writer, humorist (Mr. Dooley)
- Stuart Dybek, author
- Roger Ebert, film critic
- Dave Eggers, writer, editor, publisher
- James T. Farrell, writer
- Kenneth Fearing, poet, writer
- Edna Ferber, author, playwright
- Leon Forrest, writer
- Henry Blake Fuller, writer
- Larry Gelbart, comedy writer
- John Gunther, writer
- E. Gary Gygax, author
- Lorraine Hansberry, playwright
- Reidar Rye Haugan, newspaper publisher and playwright
- Ben Hecht, author, journalist
- Larry Heinemann, novelist
- Ernest Hemingway, writer
- Robert Herrick, novelist
- John Kass, journalist
- Anton LaVey, born Howard Stanton Levey, Writer of The Satanic Bible, founder of The Church of Satan
- Ann Landers (Esther Pauline Friedman Lederer), columnist
- Adam Langer, novelist
- Leo Lerner, newspaper publisher, founder of Lerner Newspapers
- Tom Mandel, poet
- Merrill C. Meigs, newspaper publisher
- Susan Murphy-Milano, author, radio host, domestic violence victims' advocate
- Charles Gilman Norris, author
- Frank Norris, novelist
- Clarence Page, columnist
- Sara Paretsky, novelist
- Ed Paschke, artist
- Cissy Patterson, journalist, newspaper editor
- Frederik Pohl, author, futurist
- Henry Rago, poet and editor of Poetry Magazine from 1955 to 1969
- Mike Resnick, author
- Mike Royko, columnist
- Ernest Samuels, biographer, winner of the Bancroft Prize and the Pulitzer Prize for Biography or Autobiography
- Carl Sandburg, poet
- Dan Savage, columnist
- Sandra Seaton, playwright and librettist
- Sidney Sheldon, playwright, screenwriter, novelist
- William L. Shirer, journalist and historian
- Shel Silverstein, poet, songwriter, and children's writer
- Gene Siskel, film critic
- Dejan Stojanović, poet, writer, essayist, philosopher, businessman, and former journalist
- Alfred Szklarski, a Polish author of youth literature
- Studs Terkel, broadcaster, author
- James Tiptree, Jr., author
- Irving Wallace, writer
- Gene Wolfe, author
Listing From Wikapedia http://en.wikipedia.org/wiki/List_of_people_from_Chicago