Here's a another tale of a helicopter-related prison break:
During the 1970s, Ireland (specifically ~~Northern Ireland~~ northern province of Ulster) entered a period of conflict known as 'The Troubles.' The conflict was mostly concentrated in the north but occasionally would spill into the rest of Ireland. One notable (and devastating) example was the dual car bombings in Dublin and Monaghan in 1973. But the funniest episode of 'The Troubles' would also happen in the Republic that same year.
Because of the violence in the north, the Irish government took steps to stop activity related to Republican (not the American GOP kind) paramilitaries such as the Provisional IRA and their smaller and more openly communist rival INLA. This was in spite of a sympathetic population. The party Fine Gael came to power with an anti-crime promise (sound familiar?) and another promise to put a stop to all paramilitary activity in the country.
On the morning of Halloween, 1973, the IRA hijacked a helicopter and told its pilot to fly towards a prison on the outskirts of Dublin called Mountjoy. The helicopter landed in the prison yard and, despite the commotion, were able to secure the IRA members that were intended for the escape. This led to a large a manhunt involving both the police and the military. Two of the men were recaptured not long after but one of them wouldn't be recaptured until 1977 - a whole 5 years later!
Libre Office.