Factual error: In Derailed, the train that Lucinda and Charles ride is called the "Red Line, to Union Station". The Red line in Chicago does not go to Union Station and the train they are on is a Metra suburban mass transit train. The Red Line is part of the "El" system and is part of the CTA, not Metra.
Derailed (2005)
Plot summary
Directed by: Mikael Hafstrom
Starring: Jennifer Aniston, Clive Owen, Vincent Cassel, Melissa George, Addison Timlin
Charles (Clive Owen) is worn down by his home life where he and his wife struggle to cope with the demands their daughter's illness, and his job. When he meets Lucinda (Jennifer Anniston) on the train to work in Chicago, there is an immediate spark between them. Soon they are doing lunch; dinner and drinks follow. This leads to an adulterous rendezvous in an hotel. But no sooner have they torn each others' clothes off than their room is invaded by a thief (Vincent Cassel) who beats Charles and rapes Lucinda. Because of the illicit nature of their relationship, Charles is reluctant to go to the Police and soon finds himself powerless to resist the every demand of the thief.
More mistakes in Derailed
Winston Boyko: Hey Chaz, you feeling ok?
Charles Schine: Yeah, I'm ok.
Winston Boyko: You sure? You look like you comin' down with that bug or somethin'.
Charles Schine: It's nothing.
Winston Boyko: Nothing? That's what Dick Lumberg said.
Charles Schine: Who's Dick Lumberg?
Winston Boyko: Nobody. That mother fucker's dead.
Answer: I assumed that that Charles Shine did not have time to return the money to the work account before his boss discovers it is gone because the banks would have been closed when he was at the hotel and retrieved the briefcase with the $100,000. Granted, prior to this he asks his boss for a check for the commercial expense, so it might have made more sense to ask for a transfer earlier because a check implies that he did not signing for funds and could not have embezzled the funds. How he stole it if he did not have access to the account, I do not know.