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The team trace Flynn to 1780 and discover that he plans to use Benedict Arnold to get to Rittenhouse... and kill him. Now the trio must decide whether they will help Flynn or hinder him.
Following a photo from the warehouse raid, the team travels back to 1934 to discover why Flynn is interested in a particular bank and a necklace key. Wyatt and Lucy end up teaming with Bonnie and Clyde, who are robbing the bank... and Bonnie has the key on her neck. Meanwhile, Denise begins an investigation into Connor.
Rufus and Wyatt track Flynn and his captive Lucy to the 1893 Chicago World Fair. However, Flynn, anticipating their arrivals, sends them to the World's Fair Hotel: the "Murder Hotel" of serial killer H.H. Holmes.
When an experimental time machine is stolen, a history professor, a soldier and an engineer are tasked with capturing the culprit. They soon learn that the thief plans to rewrite American history, and that each of them has a connection to his plan as well as the mysterious organization that funded the machine's development.