Set in Depression-era America, A Long Way From Chicago is a novel comprised of interconnected short stories. In them, the narrator, Joe Dowdel, recalls the outrageous situations he and his younger sister, Mary Alice, got into over the course of the seven summers they traveled from their home in Chicago to stay with their eccentric Grandma Dowdel in small-town southern Illinois. Though at first the siblings aren’t too thrilled to leave their Chicago friends behind to spend a week in the country, they soon realize that Grandma’s rural town—and most of all Grandma—is anything but boring.
In “Shotgun Cheatham’s Last Night Above Ground” (which describes the summer of 1929, Joey and Mary Alice’s first summer at Grandma’s), a big-city newspaper sends a “stringer” (a reporter) to Grandma’s town to investigate the origins of the recently deceased Shotgun Cheatham’s nickname. Though the story of how Shotgun got his name isn’t that interesting, locals spread all kinds of salacious rumors about it. When the stringer approaches Grandma for comment, she decides to teach the stringer (and her nosy neighbors) a lesson about meddling in other people’s business and arranges for Shotgun’s body to be on display at her home prior to his burial. When a bobcat sneaks inside the casket and makes it appear as though Shotgun’s corpse has been reanimated, Grandma shoots the apparently resurrected Shotgun “dead,” scaring the daylights out of her neighbors and the stringer—and teaching them all a valuable lesson about minding their own business.
In “The Mouse in the Milk,” the notorious Cowgill boys, sons of local dairy farmer Mr. Cowgill, blow up Grandma’s mailbox with a cherry bomb in the middle of the night. After the boys target Grandma’s neighbor Mrs. Wilcox, Grandma concocts a sneaky and convoluted plan to ensure that the boys see justice for their misdeeds. After catching them in the act of breaking into her house, she shows Mr. Cowgill (fabricated) evidence of milk the youngest Cowgill, Ernie, supposedly slipped in her milk bottle. Mr. Cowgill beats the boys as punishment, ensuring that they change their ways.
“A One-Woman Crime Wave,” takes place at the height of the Great Depression, and the local sheriff has posted a notice that warns drifters riding the rails in search of food and employment that they are not to stop in town. Grandma trespasses on private property and takes Joey and Mary Alice fishing in the sheriff’s own boat, which she borrows without asking (though she always puts it back where she found it). Downstream, they encounter the sheriff and his men—drunk, in the middle of the day. After (illegally) trapping catfish, Grandma and the kids deliver their catch to Aunt Puss, an elderly woman Grandma worked for as a girl who has fallen on hard times. After that, they return home and defy the sheriff to feed all the hungry drifters.
In “The Day of Judgment,” Mrs. Weidenbach, the wealthy and rather self-absorbed wife of local banker Mr. Weidenbach, convinces Grandma to enter her famous gooseberry pie in the County Fair. Grandma’s confidence falters when she sees Mr. Rupert Pennypacker has also entered a gooseberry pie in the competition, and she swaps the two pies at the last minute—only for Grandma’s pie (which the judges believe is Rupert’s) to win after all. Her mistake nearly costs Joey his free ride in Barnie Buchanan’s plane, the prize guaranteed to blue-ribbon winners, but she persuades Buchanan to give her grandson his ride in the end.
In “The Phantom Brakeman,” Grandma tells the kids about the “Phantom Brakeman,” a railroad worker who died in an accident whose spirit supposedly haunts the stretch of train tracks near Grandma’s home. Joey starts calling himself Joe, deeming “Joey” too childish a nickname now that he’s older. Mary Alice befriends 17-year-old Vandalia Eubanks, the shy daughter of cruel and overbearing Miz Eubanks, and secretly hides the young woman at Grandma’s house as part of a larger plot for Vandalia to hop aboard the train and elope with Junior Stubbs (the lovers come from different class backgrounds, and their families don’t approve of the relationship). In the end, the ghostly appearance of the Phantom Brakeman (Joe in disguise, seemingly acting under Grandma’s direction) distracts everyone long enough for the couple to board the train and escape to freedom.
“Things with Wings” begins with Grandma bidding Mrs. Wilcox farewell after the bank forecloses on the poor widow’s home, leaving her with no choice but to move in with her sister. Refusing to let this injustice stand, Grandma orchestrates a blackmail scheme involving forged historical artifacts, outsmarting the banker Mr. Weidenbach until he relents and agrees to return Mrs. Wilcox’s house to its rightful owner.
In “Centennial Summer,” Grandma’s town is celebrating the 100-year anniversary of its settlement. Though Grandma feigns indifference to the festivities, she can’t resist the opportunity to outdo her nemesis, Mrs. Weidenbach, in the Centennial Celebration’s various competitions—a feat she accomplishes with the help of skilled dancer Mary Alice (who beats Mrs. Weidenbach’s nephew in the talent show) and the ancient Uncle Grady (who steals Mrs. Weidenbach’s father’s title of “oldest settler in the community,” though Grandma’s claim that Uncle Grady is 103 years old is rather suspect).
“The Troop Train” skips ahead to 1942, by which point Joe and Mary Alice have grown up. World War II breaks out, and Joe enlists. The train he is to take to basic training will pass by Grandma’s house, and he sends her a telegram to let her know when to expect him, though the train won’t stop in town. Sure enough, as the train passes by Grandma’s house, Joe sees her waving as the train cars pass by. He waves back as her home fades into the distance.