Chickering received his doctorate in 1968 at Stanford University, where he studied with Gordon A. Craig. Imperial Germany and a World Without War: The Peace Movement and German Society, 1892-1914, published in 1975, was based on his dissertation.
Associate Professor of History, University of Oregon, 1974–81
Assistant Professor of History, University of Oregon, 1968–74
Instructor of History, Stanford University, 1967–68
Chickering retired from Georgetown University in 2010. While he began his career as a historian focusing on the German Empire, his interests increasingly migrated to the First World War. During his career, he published multiple monographs, edited volumes, and articles.