Chicago Sketches is a collection of seventy-two essays on Chicago history. The essays are arranged according to subject and, within each category, further divided into chronological order. There are sections devoted to early Chicago, radicals and reformers, literary institutions, neighborhood life, law and disorder, spirituality, politics, disasters and events, the art, visitors, and sports and recreation.

The book contains a dozen maps and fifty-one black-and-white photographs. The appendix provides a chronology of major events in Chicago history and a listing of Chicago mayors and historic landmarks and districts. An annotated bibliography offers suggestions for further reading.