A Long Way from Chicago by Richard Peck, 1998.
Joey and Mary Alice live in Chicago during the Great Depression, but every summer, they go to stay with their grandmother in a small town in Illinois. At first, the kids think that staying with their grandmother will be boring, but they soon find out that Grandma is anything but. She’s an eccentric woman who doesn’t let anyone boss her around and doesn’t have much respect for any rules but her own. Although she’s pretty tough, Joe and Mary Alice learn that, deep down, Grandma really does care about other people and tries to help them, even though she often gets into a lot of trouble in the process. Each chapter is a short story from each of the summers that the kids spend with their grandmother, from 1929 to 1935:
Shotgun Cheatham’s Last Night Above Ground (1929): When a reporter comes looking for information about a recently deceased local character, Grandma volunteers to hold a wake for him in order to teach everyone a lesson about truth and gossip.
The Mouse in the Milk (1930): When a group of local pranksters needs to be punished, Grandma decides to play a little trick of her own to get even.
A One-Woman Crime Wave (1931): Grandma turns to trespassing and illegal fishing in her quest to feed the hungry.
The Day of Judgment (1932): Grandma enters a baking contest at the county fair for the glory of her home town and a chance to ride in an airplane.
The Phantom Brakeman (1933): Mary Alice tries to help a young woman escape from her abusive mother, and Grandma brings a ghost story to life for the sake of young love.
Things with Wings (1934): Effie Wilcox, a neighbor of Grandma’s, loses her house to the bank, but Grandma comes to the rescue by demonstrating the power of rumors.
Centennial Summer (1935): As Grandma’s town celebrates its centennial, Grandma decides that uppity Mrs. Weidenbach, the banker’s wife, needs to be taught a lesson.
The Troop Train (1942): Joe, now much older, has enlisted in the Army Air Corps during World War II. As the train taking him to his basic training passes Grandma’s town, she’s there to wave to him.
During the course of the stories, the author includes details about how Prohibition and the Great Depression affected people and other details about life in the early 1930s. This book is a Newbery Honor Book.