St. Louis, Missouri. 1933
At the height of the Great Depression, eighth grade student Aaron Kurlander (Jesse Bradford) presents a writing assignment about his hero, pilot Charles Lindbergh who flew solo across the Atlantic Ocean in 1927. After school, Aaron chastises his younger brother, Sullivan (Cameron Boyd), for attempting to steal another child's dessert.
At the fleabag Empire Hotel where they live, Sullivan begs Aaron to teach him how to play marbles, and the older boy reluctantly gives him a few to practice with. Upstairs, the boys return to their room to learn that Sullivan will be sent to stay with their uncle until their father, Eric (Jeroen Krabbé), can get a job selling watches and save enough money to move into an apartment.
Back at school, Aaron saves wealthy student Billy Thompson (Chris Samples) from being bullied by challenging the tormentors to a game of marbles. He easily defeats them, and Billy invites Aaron to his house in a gesture of gratitude. There, Billy shows Aaron his collection of canaries and offers him a female to mate with his own bird, Skippy. Reluctant to admit his father's lowly profession, Aaron tells Billy and his mother, Mrs. Thompson, that he flies airplanes for the government.
At school, Aaron's teacher, Miss Mathey (Karen Allen), notices that the Kurlander's address is no longer current and asks the boy for his new residence. Again reluctant and embarrassed to tell the truth that his family is homeless and residing in a hotel, Aaron provides a false location and name, claiming that his father works for the government, but Miss Mahey learns the truth when she follows him home.
Later, Mrs. Kurlander (Lisa Eichhorn) reveals that she must return to a sanitarium for treatment of her worsening tuberculosis. Over the weekend, Aaron joins his older friend, Lester Silverstone (Adrian Brody), working as a golf caddie, but the job does not go well and Lester tells him to return home.
At the hotel, a shy neighbor teenage girl named Ella McShane (Amber Benson) invites Aaron over for food and asks him to dance to some radio music, but she suddenly collapses in an epileptic fit.
That evening, with his mother away, Aaron prepares tomato soup for himself and his father using ketchup and hot water.
One afternoon, Aaron recruits Lester to help him move his father's illegally parked car before the inquisitive Patrolman Burns (John McConnell) has it ticketed. Once Lester pushes the vehicle, Aaron fails to pump the brakes and it rolls down a steep street, narrowly avoiding a boys' stick-ball game and oncoming traffic. Lester catches up with him when the car finally stops, and the boys return to the hotel. Mr. Kurlander announces he has taken a job as a traveling watch salesman, forcing him to miss Aaron's junior high school graduation the upcoming week.
Now completely alone, Aaron is without food and decides to sell his newly-hatched canaries to a pet store. Although he expects to earn $3 per bird, the pet shop owner claims the brood consists of only females, which are deemed worthless because they cannot sing, and only gives him 50 cents. Using his last fifty cents, Aaron buys a kitten for Ella, who is recovering from another seizure.
At school, he steals a sandwich from a gluttonous boy, prompting the wealthy Christina Sebastian (Katherine Heigl) to invite him to her graduation dinner after Billy Thompson's party. Upon realizing that his only suit jacket is too small, Lester takes Aaron to the storage room, where they steal items that have been repossessed from former tenants.
On the day of the graduation, Aaron dresses in his new suit and Ella kisses him goodbye before her family moves to Illinois so she can get better treatment for her epilepsy. During the ceremony, he is shocked to be the recipient of an award for demonstrating good character. Afterward, at Billy's party, Aaron invents an elaborate excuse for why his parents did not attend graduation, and gossip quickly spreads. Aaron overhears a peer calling him a "charity case" who receives special treatment from the teachers. When Billy confronts him about his lies, Aaron flees the party and returns home to the hotel.
At the Empire Hotel, Aaron discovers an eviction notice under the door because his father has failed to pay the rent. Although sympathetic, the hotel owner insists the bank will throw the Kurlanders out within three days. Aaron visits the sanitarium and yells up to his mother in her cell, but is unable to tell her the bad news.
On his way home, he spots a former Empire Hotel resident now living in a nearby Hooverville (shanty town). Desperate, he visits his neighbor, Mr. Mungo, offering to sell his cigar band collection. Mr. Mungo understands Aaron's predicament and offers to speak to the hotel owner on his behalf. Later, Aaron forges a letter to his uncle requesting that Sullivan be sent home.
The next morning, Aaron awakens to the sounds of a riot as the police raid the impoverished camps set up outside. Lester is arrested, but gives Aaron a prized pocketknife. Aaron rushes back inside before the hotel's malicious bellhop prematurely locks him out of his room. When Mr. Mungo leaves Aaron a note containing a new cigar band for his collection, Aaron attempts to thank him, but notices water and blood oozing from under his neighbor's door. He walks into the apartment and discovers that Mr. Mungo has slit his wrists in a suicide.
After finishing the last of his stale dinner rolls, Aaron arranges magazine images of food on a plate and eats them. Later, he becomes ill and hallucinates the traumatizing events of the past few weeks. When he recovers, he curses his father and falls asleep again, only to be awakened by Sullivan knocking at the door. The boys tearfully hug and gorge on Sullivan's food that he brought with him until their father unexpectedly arrives. Overjoyed to see them, he announces that he got a new job as a clerk for the Works Progress Administration, which pays a $65 monthly salary. Mr. Kurlander suggests he avoid paying the outstanding hotel bill of $174 by leaving their belongings behind when they move to their new apartment, but Aaron refuses. He and Sullivan lower their suitcases out the window with a rope, packing everything but the suit Aaron and Lester stole, into their car. Sneaking into the basement storage room, Aaron retrieves a box of watercolor paints to return to the evicted tenant now living in the shanty down. While still in the basement, Aaron also locks all of the padlocks that the bellhop uses to lock deadbeat tenants out of their rooms and throws away the keys, leaving the padlocks useless.
In the final scene, after Mr. Kurlander picks up his recovering wife from the sanitarium, the reunited family moves into their spacious new apartment at the Carleton Court.