This journal issue presents teaching ideas based on the city of Chicago and the literary works of its citizens. The first article describes a combined social studies/English course based on the study of Chicago's influence on literature and history. Included is a course outline with required readings, class activities and assignments, an assessment of the strengths and weaknesses of the course, a list of twentieth-century Chicago fiction writers, and assignments based on the presidential election of 1860. The second article describes how Carl Sandburg's poems can be used to study the question, "What does Chicago mean?" and to teach students how to read dramatically. The final article examines the song lyrics of Chicagoan Steve Goodman, and discusses the relevance of Goodman's songs to Chicago places and people and how they illustrate the effectiveness of precise detail and apt metaphor. In addition, it offers suggestions showing how popular songs can be used to demonstrate the writing modes composition teachers want students to understand. (HOD)