Not long after starring in Las Vegas Shakedown, Dennis O'Keefe headed eastward to appear in Chicago Syndicate. This time, O'Keefe is cast as honest accountant Barry Amsterdam, determined to get the goods on Windy City gangster boss Arnie Valent (Paul Stewart). Insinuating himself into Valent's confidence, Amsterdam quietly begins gathering evidence. For a while it looks as though Amsterdam will go the way of his predecessor in Valent's operation, who ended up sleeping with the fishes, but in films of this nature justice usually prevails.