Klaus (Joseph Morgan) and Stefan (Paul Wesley) arrive in Chicago, where Stefan is reunited with a vampire (guest star Claire Holt, "Pretty Little Liars") who hasn't really moved on from her interest in him decades earlier. In a flashback to Chicago in the 1920s, Stefan comes face-to-face with a shocking chapter from his wild past. After Damon (Ian Somerhalder) gets a tip on Stefan and Klaus' whereabouts from an unexpected source, he and Elena (Nina Dobrev) follow their trail. Back in Mystic Falls, Tyler is concerned about Caroline and turns to Sheriff Forbes (guest star Marguerite MacIntyre) for help.
