| | Preface | p. 15 |
| | Discovery | p. 27 |
| | The Priest and the Explorer | p. 27 |
| | Joliet's Dream | p. 41 |
| | "Didn't Expect No Town" | p. 48 |
| | Wild Chicago | p. 48 |
| | Banishing the Past | p. 58 |
| | Odgen's Chicago | p. 66 |
| | The Founder | p. 66 |
| | A Prairie Aristocracy | p. 76 |
| | The Grid and the Balloon Frame | p. 81 |
| | The Great Chicago Exchange Engine | p. 89 |
| | The Big Junction | p. 89 |
| | The Mechanical Man | p. 103 |
| | Stacker of Wheat and Wood, Packer of Pork | p. 106 |
| | Empire City of the West | p. 122 |
| | Chicago Against Nature | p. 122 |
| | City of Extremes | p. 131 |
| | My Lost City | p. 143 |
| | The Great Fire | p. 143 |
| | Unapproachable in Calamity | p. 158 |
| | That Astonishing Chicago | p. 179 |
| | "Grander and Statelier Than Ever" | p. 179 |
| | America's City | p. 188 |
| | The Chicago Machine | p. 198 |
| | Empires of Order and Blood | p. 198 |
| | A Fortress of Oppression | p. 216 |
| | The Pullman Idea | p. 224 |
| | Steel Rails to Country Kitchens | p. 240 |
| | The Streetcar City | p. 254 |
| | Palaces of Desire | p. 254 |
| | The Loop | p. 265 |
| | City and Suburb | p. 273 |
| | Sunday in Chicago | p. 294 |
| | Stories in Stone and Steel | p. 301 |
| | Something New Under the Sun | p. 301 |
| | Burnham and Root | p. 314 |
| | The Major's Birdcage | p. 335 |
| | Factories in the Sky | p. 347 |
| | Sullivan and Civic Renewal | p. 354 |
| | The Auditorium | p. 354 |
| | A Proud and Soaring Thing | p. 366 |
| | The New Chicago | p. 378 |
| | Burnham's White City | p. 378 |
| | Hutchinson's Three-Ring Circus | p. 385 |
| | Harper's University | p. 393 |
| | The Social Defense of Caste | p. 404 |
| | The New Chicago Woman | p. 413 |
| | Cleansing the City | p. 423 |
| | The Battle for Chicago | p. 435 |
| | Politics "Ain't Bean Bag" | p. 435 |
| | Why the Ward Boss Rules | p. 452 |
| | Haymarket | p. 468 |
| | It's Harrison Again | p. 482 |
| | 1893 | p. 488 |
| | The Fair | p. 488 |
| | The "Gomorrah of the West" | p. 505 |
| | Stories of the Streets and of the Town | p. 516 |
| | After the Fair | p. 533 |
| | If Christ Came to Chicago! | p. 533 |
| | Regeneration | p. 542 |
| | Notes | p. 555 |
| | Bibliography | p. 639 |
| | Acknowledgements | p. 683 |
| | Index | p. 685 |