- “Boss” by Mike Royko: This biography explores the life and political influence of Richard Daley, one of the most powerful mayors in American history. Royko paints a vivid picture of Chicago’s neighborhoods while revealing how Daley built and wielded political power.
- “Humboldt’s Gift” by Saul Bellow: This Pulitzer Prize-winning novel follows a washed-up writer named Charlie Citrine as he navigates middle-age, Jewish identity, and success. Set in Chicago, the story combines introspection with madcap farce, capturing elements of the city’s character.
- “The Warmth of Other Suns” by Isabel Wilkerson: Although not solely focused on Chicago, this influential book discusses the great migration of African-Americans from the South to northern industrial cities, including Chicago. Wilkerson explains how this migration reshaped the city and its impact on urban life.
- “Fire on the Prairie” by Gary Rivlin: This book delves into the election of Harold Washington, Chicago’s first black mayor, in 1983. Rivlin explores the challenges Washington faced while contending with a hostile city council, demonstrating the impact of his victory on Chicago’s political landscape.
- “Every Goddamn Day” by Neil Steinberg: A collection of anecdotes tied to Chicago, this book offers insight into the city’s history. From monumental moments like Washington’s mayoral victory to more ephemeral entries, Steinberg captures the essence of Chicago’s past.
- “Chicago: City On The Make” by Nelson Algren: As a long-form poem, Algren’s book traces the foundation of Chicago and its evolution until 1951. Describing the city as a frontier town built by hustlers, Algren’s words reflect an earlier era in Chicago’s history, highlighting its unique character and spirit.
Wanderlist: Six great books about Chicago
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