America's Second City abounds in literary talent, and this anthology spotlights writers associated with Chicago as well as tales that take the Midwestern metropolis as their setting. Contributors include Richard Wright, Saul Bellow, James T. Farrell, Edna Ferber, Zane Grey, and many others.

George Ade's "The Judge's Son" offers a brief character sketch in which two down-and-outers find solace in their shared suffering; "From A to Z," by Susan Glaspell, recounts an idealistic young woman's pursuit of a glamorous publishing job on Michigan Avenue; Will J. Cuppy's "The Extra Major" profiles a struggling freshman at the University of Chicago; and "Reform in the First" presents Brand Whitlock's study of Chicago politics. Additional stories include Nelson Algren's "A Bottle of Milk for Mother"; "The Fall of Edward Barnard" by W. Somerset Maugham; Stuart Dybek's "Chopin in Winter"; and other moving and thought-provoking tales.