Jail Break (Skyrim)

Whiterun
Once you do a crime and the guards catch you, you can choose to end up in the prison, or the so called Dragonsreach Dungeon. Once you are inside your cell, you got nothing but rubbish clothes and a single picklock. There are two possible ways to escape from the prison. The first one is shorter but very riskier. When there is no guard on sight, use your skills to lockpick the main door of cell, which has an Adept level of lockpicking. Then you must search for your equipment, it could be in any chest inside the room, but watch out as a guard patrols the area. Once you get your equipment if you manage to, you must carefully escape through the main door, because there are few guards patroling there too. The other way of escaping is a lot longer, safer, but it's still not that easy. In your cell there will be always a dead bandit lying on the ground. Pull him off the ground, and you will see a hatch door with Novice lock. Open it and you will fall into the sewers, deeper into the dungeon. It's a long way, and guards will always patrol these areas, and of course this is more interesting than the other aggresive way of escaping. Once you reach the end of the severs, you will reach the Guard Barracks. People are allowed to enter in the Guard Barracks, so Guards there will think you are just an ordinary traveller. But keep far distance with the guards, because if you get too close to them, they will realize you and you will end up back in jail. Once you exit the Guard Barracks, you are outside of Whiterun. Now, you must not get close to any people or any guards, as they will instantly remember on you. Go to Dragonsreach, recover your equipment, don't go in Whiterun for few days, and the guards will forget you, and of course, your bounty will be cleared.