"A Long Way From Chicago" follows two siblings, Joey and Mary Alice Dowdel, as they spend time away from their Chicago home every August when they visit their grandmother in a small town. The book has eight chapters, with each chapter taking place during the August of a different year. The first seven stories take place from 1929 to 1935, and the final chapter takes place in 1942.
The first chapter is "Shotgun Cheatham's Last Night Above Ground." Joey is 9 and Mary Alice is 7. A resident of the grandmother's town, named Shotgun Cheatham, has died. A local reporter writes a story about him while the grandmother holds an open house for him.
In "The Mouse in the Milk," a group of boys terrorize the grandmother's town, so she outsmarts them and gets them in trouble with their father. The next chapter, "A One-Woman Crime Wave," has the grandmother catching catfish illegally and feeding the hungry. "The Day of Judgment" features a pie baking contest at the county fair.
In "The Phantom Brakeman," Mary Alice helps a new friend of hers run away to elope. "Things With Wings" has the grandmother tricking a banker into giving another resident her foreclosed house back. "Centennial Summer" details the town's centennial celebration.
"The Troop Train" takes place seven years later. Joey enlists in the army air corps to fly planes and fight in World War II. He sends a message to his grandmother, telling her he is going to pass through her town. She waves to each car, and Joey waves back.