"I used to go to jail."
Translation:Tôi đã từng bóc lịch.
Not sure if this is what the Vietnamese sentence is trying to go for, but in English, the "used to" construct usually implies a habitual action.
So, I would assume either this person used to work in the prison as a guard or a warden, OR this person kept getting arrested, put in jail, paroled/released and then started this vicious cycle all over again.
Also 'go to' when used like this implies going voluntarily (people are usually 'sent to' jail; you only usually say 'go to jail' when talking about sentence length - 'he went to jail for 5 years')
Plus, 'used to' implies a change in the action - you don't do it anymore.
The only way I can think this sentence would sound natural - 'I used to go to jail' - is if 'jail' was the name of a trendy club or something: 'I used to go to Jail but then they changed the music; now I go to Heaven.'