In St. Louis, Missouri, 1933, during the height of the Great Depression, Aaron Kurlander (Jesse Bradford), an eighth-grade student, excitedly shares a writing assignment about his idol, the aviator Charles Lindbergh, known for his solo transatlantic flight in 1927. After school, Aaron reprimands his younger brother, Sullivan (Cameron Boyd), for trying to steal another child's dessert.
At the rundown Empire Hotel, where they reside, Sullivan pleads with Aaron to teach him how to play marbles, and although hesitant, Aaron gives in and offers him a few marbles for practice. Upon returning to their room, the boys learn of Sullivan's impending stay with their uncle until their father, Eric Kurlander (Jeroen Krabbé), secures a job selling watches and can afford a better living situation.
At school, Aaron comes to the defense of wealthy student Billy Thompson (Chris Samples) by challenging the bullies to a game of marbles, which he wins effortlessly. Grateful, Billy invites Aaron over to his house, revealing his collection of canaries and offering one to mate with Aaron’s bird, Skippy. Eager to hide his family's financial struggles, Aaron fabricates a story about working for the government.
However, his teacher, Miss Mathey (Karen Allen), notices discrepancies in Aaron’s address and unravels the truth of his homelessness. During this time, Mrs. Kurlander (Lisa Eichhorn) discloses her need to return to a sanitarium for treatment of her escalating tuberculosis. As the weekend approaches, Aaron attempts to help his older friend, Lester Silverstone (Adrian Brody), in a golf caddying job, which leads to disappointing results.
In an unexpected turn, a quiet neighbor girl, Ella McShane (Amber Benson), invites Aaron to join her for dinner and they share a dance, but she suffers an epileptic seizure, leaving him distressed. That night, Aaron tries to prepare a meal for himself and his father using ketchup and hot water to make tomato soup.
One day, Aaron teams up with Lester to avoid having their father’s illegally parked car ticketed, but chaos ensues when the car rolls down a hill, narrowly missing a game of stick-ball. With newfound responsibilities, Mr. Kurlander announces a job as a traveling watch salesman, compelling him to miss Aaron's junior high graduation the following week.
Left to fend for himself, Aaron sells his new canaries to a pet shop, only to discover they are all females and thus worthless, netting him a meager fifty cents. He spends this money on a kitten for Ella, who is recovering from another episode. At school, Aaron steals a sandwich and is subsequently invited to a graduation dinner by Christina Sebastian (Katherine Heigl), contributing to his growing web of lies.
On the day of his graduation, as Aaron dons his new suit, he shares an emotional goodbye kiss with Ella. During the ceremony, to his surprise, he receives an award for good character. Afterward, while fabricating excuses for his parents' absence at the celebration, Aaron overhears unkind comments branding him a "charity case." This leads him to flee from Billy's party, returning to the hotel, where he finds an eviction notice due to unpaid rent.
Despite his attempts to deliver bad news to his mother at the sanitarium, events spiral as he encounters a former tenant now living in a nearby Hooverville. Aaron, in desperation, offers his cigar band collection to a supportive neighbor, Mr. Mungo. Tragically, he later discovers Mr. Mungo has committed suicide.
In a state of despair, Aaron resorts to arranging magazine images of food, pretending to eat, which sends him into a hallucination from the intense stress he has been under. Eventually, he is stirred from his daze by Sullivan's arrival, and they indulge in the food he’s brought. The reunion is short-lived, as their father unexpectedly returns with news of his new job as a clerk for the Works Progress Administration, earning a modest salary.
Despite his father's suggestion to abandon their belongings and the outstanding hotel bill, Aaron stands firm. He and Sullivan lower their suitcases from the window while also stealing back watercolor paints to return to the evicted tenant. In a bold act against the hotel's oppressive bellhop, Aaron locks away the padlocks used against struggling tenants.
In a heartwarming conclusion, the reunited Kurlander family moves into their new apartment at the Carleton Court, finally finding some stability amidst the adversity that once tore them apart.
