In 1933, John Dillinger (Johnny Depp) is brought to the Indiana State Prison by his partner John "Red" Hamilton (Jason Clarke), under the guise of a prisoner drop. They overpower several guards and free members of their gang including Charles Makley (Christian Stolte), Homer Van Meter (Stephen Dorff), Walter Dietrich (James Russo), Ed Shouse, Jr. (Michael Vieau), and Harry Pierpont (David Wenham). A shootout starts after Shouse beats a guard to death; Dietrich is killed, and Dillinger kicks Shouse out of the car as they flee. The rest of the gang retreats to a farm house hideout, where crooked East Chicago, Indiana, police officer Martin Zarkovich (John Michael Bolger) convinces them to hide out in Chicago, where they can be sheltered by the local Mafia. After killing Pretty Boy Floyd (Channing Tatum), Bureau of Investigation agent Melvin Purvis (Christian Bale) is promoted by J. Edgar Hoover (Billy Crudup) to lead the hunt for Dillinger, declaring the first national "War on Crime". Purvis shares Hoover's belief in using scientific methods to battle crime, ranging from cataloging fingerprints to tapping telephone lines.
In between a series of bank robberies, Dillinger meets Billie Frechette (Marion Cotillard) at a restaurant and proceeds to woo her by buying her a fur coat. Frechette falls for Dillinger even after he tells her who he is, and the two quickly become inseparable.
Purvis leads a failed ambush at a hotel where he believes Dillinger is staying; an agent is killed by Baby Face Nelson (Stephen Graham) with Tommy Carroll (Spencer Garrett), who escape. After this incident, Purvis requests that Hoover bring in professional lawmen who know how to catch criminals dead or alive, including Texas "cowboy" Charles Winstead (Stephen Lang).
Police find Dillinger and arrest him and his gang in Tucson, Arizona, after a fire breaks out at the Hotel Congress. Purvis arrives that evening and briefly talks with Dillinger, who is subsequently extradited to the Lake County Jail in Crown Point, Indiana, where he is locked up by Sheriff Lillian Holley (Lili Taylor) pending trial. Dillinger, with a fake gun, and other inmates later escape the jail in Holley's own cruiser. Dillinger is unable to see Frechette, who is under tight surveillance. Dillinger learns that Frank Nitti's (Bill Camp) Chicago Outfit associates are now unwilling to help him because Dillinger's crimes are motivating the federal government to begin prosecuting interstate crime, which imperils Nitti's bookmaking racket.
Carroll goads Dillinger into a bank robbery in Sioux Falls, promising a large score. Despite Dillinger's dislike for Baby Face Nelson, who will be involved, he participates. A shootout triggered by Nelson shooting a cop occurs during the robbery; Carroll is wounded and left for dead. They retreat to the Little Bohemia Lodge in Manitowish Waters, Wisconsin, where they to find that their haul is less than what they expected. Dillinger expresses hope he can free the rest of his gang still in prison, including Pierpont and Makley, but Red convinces him this is unlikely to happen.
Purvis and his men apprehend Carroll and torture him to find the rest of the gang's location. Purvis subsequently organizes an ambush at Little Bohemia. Dillinger and Hamilton escape separately from Nelson and the rest of the gang. Agents Winstead and Hurt (Don Frye) pursue Dillinger and Hamilton through the woods on foot, engaging them in a gunfight in which Hamilton is fatally wounded. Trying to escape along the road, Nelson, Shouse and Van Meter hijack a Bureau car, killing Purvis's partner Carter Baum (Rory Cochrane) in the process. After a car chase, Purvis and his men kill Nelson and the rest of the gang. Hamilton dies later that night and Dillinger buries his body.
Dillinger manages to meet Frechette, telling her he plans to commit one more robbery that will pay enough for them to escape together. However, when Dillinger drops her off at a tavern that he thinks is safe, she is captured by law enforcement. Frechette is beaten during an interrogation to learn Dillinger's whereabouts, which she does not reveal; Purvis and Winstead stop the interrogation. Meanwhile, Dillinger meets with Alvin Karpis (Giovanni Ribisi), who tries to recruit Dillinger in a train robbery with his associates, the Barker Gang. Dillinger agrees to participate and intends to flee the country the next day. Dillinger receives a note from Billie through her lawyer, Louis Piquett (Peter Gerety), telling him not to try to break her out of jail, but to wait until she is released to start a new life together.
Through Zarkovich, Purvis enlists the help of madam and Dillinger acquaintance Anna Sage (Branka Katić), threatening her with deportation to Romania if she does not cooperate and uses her as his spy. She agrees to set up Dillinger, who is hiding with her. Later, Dillinger and Sage see Manhattan Melodrama at the Biograph Theater. After the film ends, Purvis signals other agents upon seeing them leave. Dillinger spots the police but is shot multiple times before he can draw his gun. Winstead, who shot Dillinger through the head, listens to Dillinger's last words. Purvis departs to inform Hoover that Dillinger is dead.
Winstead later tells Frechette, still incarcerated, that he thinks Dillinger's dying words were "Tell Billie for me, 'Bye bye Blackbird.'" The closing text reveals that Melvin Purvis quit the Federal Bureau of Investigation in 1935 and died by his own hand in 1960, and that Billie lived out of the rest of her life in Wisconsin following her release in 1936.
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