I might take a chance on the iPad 1, since it's out of warrantee, but it's never broke (cross fingers). The iPad 2 and the glued on screen sounds like it would be extremely difficult to put back together right, eve if you didn't break the screen taking it apart.
All I can suggest to the OP is a dab of silicone; something that dries fairly hard. Let it fill in a bit against the case and any near components, but don't get wild. Test in on some similar plastic first, to make sure it will not damage the plastic, and that it will be hard enough to hold the jack firmly in place. That's what I would do based on my past electronics repair experience. Superglue is too un reliable and a bit to much of it would damage the jack beyond salvage.
Make sure all surfaces are clean. You might even rough them up slightly.