Coast to Coast and Back to Chicago begins with the protagonist Mick Scott hitchhiking out of the Windy City to escape a cold winter and a failed relationship with a cold-hearted woman. His trip takes him across the Deep South and up the east coast to Boston. He continues on through the west to San Francisco with stops in Austin, El Paso, Santa Fe, and Salt Lake City. He then returns to Chicago where he resolves his relationship with the woman he left while meeting the famous columnist Mike Royko, who helps him in his attempt to publish a book about his hitchhiking adventures.