Cavalry units from Midwestern states remain largely absent from Civil War literature, and what little has been written largely overlooks the individual men who served. The Fifth Illinois Cavalry has thus remained obscure despite participating in some of the most important campaigns in Arkansas and Mississippi. In this pioneering examination of that understudied regiment, Rhonda M. Kohl offers the only modern, comprehensive analysis of a southern Illinois regiment during the Civil War and combines well-documented military history with a cultural analysis of the men who served in the Fifth Illinois. The regiment’s history unfolds around major events in the Western Theater from 1861 to September 1865, including campaigns at Helena, Vicksburg, Jackson, and Meridian, as well as numerous little-known skirmishes. Although they were led almost exclusively by Northern-born Republicans, the majority of the soldiers in the Fifth Illinois remained Democrats. As Kohl demonstrates, politics, economics, education, social values, and racism separated the line officers from the common soldiers, and the internal friction caused by these cultural disparities led to poor leadership, low morale, disciplinary problems, and rampant alcoholism. The narrative pulls the Fifth Illinois out of historical oblivion, elucidating the highs and lows of the soldiers’ service as well as their changing attitudes toward war goals, religion, liberty, commanding generals, Copperheads, and alcoholism. By reconstructing the cultural context of Fifth Illinois soldiers, Prairie Boys Go to War reveals how social and economic traditions can shape the wartime experience.