Colonel Joseph L. Ryan (Sinatra) is an American pilot whose P-38 Lightning is shot down, and then is taken to a Prisoner of War camp in Italy, run by the cruel Major Battaglia (Adolfo Celi), and populated mainly by British prisoners (9 Battalion, Royal Fusiliers, 167 Infantry Brigade, 56 [London] Infantry Division [British]). As senior officer, Col. Ryan assumes command of the prisoners. The British commanding officer had recently died as a result of the harsh discipline in being put in the metal "sweat box". Ryan at first pays respect to his predecessor, Major Eric Fincham (Howard) by refusing to sit in the late commanding officer's chair. When the British attempt to flog an American prisoner (of which there are only eight) for stealing rations, Ryan discovers he was stealing medicine which Fincham has ordered be stashed for an escape attempt. Ryan orders that the drugs be dispensed as necessary. He then shows the Italians the prisoners' escape tunnels in return for their Red Cross parcels. Battaglia doesn't keep his word so Ryan then orders the prisoners to strip and burn their filthy clothes so Battaglia will have to issue new ones. Battaglia does so, but throws Ryan into the sweat box as a punishment. That night, on hearing of the Italian capitulation, the guards flee, leaving the camp unguarded. The British put Battaglia on trial as a war criminal, and allow his second-in-command and Anglo-Italian translator, Captain Oriani (Sergio Fantoni), to defend him. Battaglia portrays himself as a broken man who has repudiated fascism, and Ryan orders him not to be executed, but to be put in the sweat box.

However, the Germans return and capture them all. Fincham is furious at the incorrect thought that Oriani betrayed them, but when they are put on the train, they find a severely battered Oriani in the prisoner carriage. Battaglia is gloating outside, and they realise they have been betrayed to the Germans by the former commandant. The false impression of collaboration with the Italian guards earns Ryan the nickname "Von Ryan" from the irate Fincham. The prisoners manage to seize control of the train by dangerously escaping through the bottom of the carriage, climbing onto the roof, and strangling the guards with improvised garrotes. After taking control of the roof, at the next stop, they jump on the remaining guards, and capture the German commander of the train, Major Von Klemment (Wolfgang Preiss) and his Italian mistress, Gabriella, (Raffaella Carrà ). Oriani persuades the Italian locomotive engineer to help, and the German-speaking Allied Chaplain, Captain Costanzo (Edward Mulhare), is enlisted to impersonate the German commander to ensure their passage through the next station.

During stops as stations, Von Klemment and Gabriella are kept bound and gagged in a compartment. Gabriella conceals a piece of a broken drinking glass to cut their bonds. At one station Von Klemment escapes, shoots Orde (John Leyton), but is shot himself. Ryan, in a German uniform, then has to reluctantly shoot Gabriella as she escapes to prevent her from betraying them. Ryan then makes involuntary eye contact with a nearby Italian youth who had previously been hurling insults at what he thought were Germans and now silently stares with contempt at Ryan. By this time a German troop train has been sent in pursuit, and Von Ryan's train is attacked by three German fighter aircraft. One aeroplane is shot down, but the other destroys a section of track. The POWs then take a section of the track behind them and replace the damaged track in front of them. Meanwhile Ryan, Fincham and the others try to hold off the German soldiers. The track is repaired and the train started, and Ryan and Fincham run behind the train to get aboard. Fincham reaches the train and desperately reaches for Ryan, urging him to run faster. But Ryan is gunned down by the German commander just short of the train, which then crosses over to neutral Switzerland.

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