I saw the show on Turner Classic Movies. The plot was entertaining. It kicks off with a murder of a mob accountant who gave inside info to a newspaper man (the "Syndicate" didn't like that.) The newsman then gets some leading Chicago people plus lawmen together to try to "break the Syndicate wide open." They persuade Barry Amsterdam (Dennis O'Keefe), an aspiring accountant dreaming of starting his own business, to infiltrate the mob and get the lowdown on the crooks. He ends up doing an amazing job, for an accountant! But the use of real street scenes is what made this a very interesting movie for a Chicago history buff like me. You can see many downtown locations (theaters, buildings, bridges, rivers, street signs), era shots (men in hats, big cars, 50s trains & buses) and dialog about real places (Halsted, Ohio, The Palmer House, Maxwell Street). Lot's of fun!

The best part of "Chicago Syndicate" for me was seeing Abbe Lane and Xavier Cugat! I remember them from television and their chihuahuas. In fact, I think they fought over them in the divorce.

Dennis O'Keefe is Barry Amsterdam who goes undercover to get dirt on organized crime. An accountant has just been murdered as he was about to tell what he knew. A citizen's group sends in O'Keefe, with the promise of a $60,000 fee.

Amsterdam wins the trust of the main man (Paul Stewart), and he sets out to find his secret ledger and anything else that will serve as evidence. He meets lovely Sue Morton, who turns out to be the sister of the accountant who was killed. She joins Barry in bringing down the criminals.

In the late '40s and '50s, many films were made with a narration, as this one was. Usually they are pretty dry. This one wasn't, with some good scenes and a nice performance by O'Keefe. Abbe Lane plays the mobster's girlfriend, and she sings with. Benny Chico's (Cugat's) band. She was a knockout.

It takes a lot of patience to get past all the explanatory details at the beginning of this film that gets Dennis O'Keefe to successfully infiltrate the Chicago mob on assignment for the FBI. He begins to work closely with mob head Paul Stewart and becomes involved with two very different women involved somehow within organized crime: sensuous singer Abbe Lane and the vengeful Allison Hayes whose father was murdered at Stewart's orders. for much of the film, The two women believe that O'Keefe is Stewart's right-hand man, and he doesn't want to prove them wrong. But, it isn't before long that all of the cats are let out of the bag and betrayal takes control with O'Keefe working vigilantly to bring all of the corruption down.

Not so much a good film as a riveting one once you get past knowing the details, this does have some interesting characterizations and chilling moments where it appears that O'Keefe's identity will be exposed. Stewart and Hayes give the best performances, highlighted by vintage location photography and some thrilling chase sequences, particularly at the end. It's a rare chance to see Spanish bandleader Xavier Cugat in a role other than himself, but he really isn't given anything of consequence to do. A typically overdramatic noir narration is the predictable structure but fortunately, the dialog isn't as silly.