While Dillinger was lodged in the jail at Lima, Ohio, his companions carried out their escape on October 12. All ultimately getting away except for Joseph Jenkins, who after being thrown from the getaway car after the Michigan City jail break, managed to commandeer a vehicle driven by a youth who was able to escape after tricking Jenkins into checking the gas tank. Jenkins was later shot and killed by local posse members on alert in Beanblossom, Indiana.
Three of the escapees, Pierpont, Clark and Makley, soon broke Dillinger out of the Lima jail after badly beating and shooting Sheriff Jesse Sarber, who died that evening. Immediately after the Lima escape the gang went to Cincinnati. Later the gang proceeded to Chicago to avoid the intense manhunt throughout Ohio. In Auburn and Peru, Indiana, they robbed police arsenals acquiring a cache of weapons including machine guns and also bulletproof vests.
During the gang's stay in Chicago, several important events were to transpire. On November 15, Dillinger, with his new girlfriend, Evelyn "Billie" Frechette, narrowly escaped a police ambush set up when an informant had notified the police that Dillinger would be seeing a dermatologist named Dr. Charles Eye. Dillinger eluded his pursuers after having his vehicle shot up in a high speed chase.
The publicity mounting, on November 20, the gang carried out a daring robbery in Racine, Wisconsin. With shots being fired, they escaped behind a shield of hostages. Then on December 14, John Hamilton mortally wounded Sergeant William Shanley, when the detective tried to capture Hamilton in a garage where the detective had followed a lead on a gang vehicle being repaired there. The killing of this detective would foce the gang out of Chicago but Hamilton and Homer Van Meter were told they were not welcome to follow the gang to Florida until they settled matters with the Chicago Capone mob lead by Frank Nitti as capone was servng time in the Atlanta Federal Penitentiary.