I've always liked stories about prison breaks so I am asking the above question.
The first instalment of Strange Aeons is a kind of prison break.
(There’s an esoteric/arcane element to it though and as written the PCs all have amnesia, so it’s not “traditional”. It’s also an asylum rather than a run-of-the-mill prison...first thing that comes to mind though).
If you don't mind a 3.5 adventure, Dungeon #135 has a 10th level adventure called "Chains of Blackmaw" that's a lot of fun.
The module Midnight Mirror is sort of an inversion. The PCs have to get into a prison and break it :P
Not a module, may not pertain, but one homebrew campaign I was in started us on a ship, shackled with the slaves. The party was so spread out unless you had low light or darkvision you could see the other party members. We didn't even know each other before this voyage so we weren't looking for anyone we knew anyways.
I hate these beginnings unless I'm in a Bethesda game, I just don't trust most people to deliver like Bethesda does.
Anyways, I just kept trying to break my chains. Not that I thought I could. Or even that I thought it would do any good to be free on this boat. But it absolutely told everyone who could see or hear me that I was down to escape. So if you are smarter than tries to break his shackles man, still know I am down to escape.
The GM screwed us every way possible at every turn, and we actually still managed to escape outside of his plan.
It was awesome.
I know this has nothing to do with written modules, but if you plan for it to be fun, it can be a blast. If you try make it suck, it really sucks.
We made the best of it, felt great breaking free despite the malice of the GM. But it could have been fun the whole time if the GM wasn't purposefully being I-am-god difficult.
I don't know any modules with jailbreaks but don't be afraid to throw one in just for fun. Just make it fun.
I don't know how far back in the history of the game you are willing to go (or if you want to adapt it), but there is an AD&D 1e module titled A4 In the Dungeons of the Slave Lords that has the characters beginning in a prison cave complex that they must escape from. If you're interested, the pdf is on sale at RPGNow if you follow the link.