Jail Break (Skyrim)

This is a quick guide to escaping out of jail/prison in all the cities of. This guide describes the most direct way, and secret passages will be in short detail.

Markarth
See No One Escapes Cidhna Mine article. Basic walkthrough: Ask anyone who Madanach is and follow the questline.

After completing the mission "No One Escapes Cidhna Mine" it is impossible to ever get out without serving time. (However there is a bug in which the Dragonborn can trap themselves in Cidhna Mine forever by hitting the ore with a pickaxe, they can deplete the silver veins and since the ore does not reset after a certain amount of time; they will never be able to get the option to serve time. See the Cidhna Mine article for a fix to this bug.)

One possible way, however, is to kill Madanach and Borkul within the main area of the mine. Both of their bodies are permanent, and their keys can be stashed on them for future use.

Riften
The Dragonborn starts off in what looks more like an ill-treated hotel room than a cell. To the right there is a desk with a lockpick hidden amongst the food. Behind is the bed, and to the left is a dresser and a bucket. If they notice on the back wall, there is a shackle. Activate it andit will move the wall; revealing a tunnel. Enter them, and keep moving through the tunnels (Sometimes when activating the shackle; the wall will stay up but the guards will turn hostile and attack). Eventually there will be a sewer grate, open it and there sits the Dragonborn's confiscated items. Travel through the sewers until there is an exit. This does not work on the 360 as of patch 1.6. Firstly pick the lock of your jail cell or pickpocket it off the guard who will be standing next to the cell when the Dragonborn is jailed. Sneak towards the passageway to the left, then enter a door on the left hand side (not in front). Turn left, enter another door, and there will the confiscated belongings chest in the top right hand corner.

Exit out the same way but turn right and go through the door seen when entering the passageway. Head up the steps, turn right and there will be the door leading out to Riften.

Solitude
Solitude is perhaps the hardest of the jails to escape.

First, after being jailed, in your cell under a bucket in the corner on the left side of your door there is a lockpick which is very useful if yours breaks, turn and check the wall on the left side of the windows towards the bottom. It should say "Activate Crumbling Mortar." After activating it, the wall will crumble. Just follow the path and you will be brought to a hole in the wall from which you can access the Prisoner's Possessions box, which has a master lock. You can also loot the key off the guards once you have killed them. Be careful to wait, as guards will come through the crumbling wall and exit THROUGH your prison door, leaving it wide open. Don't go that way though. If you have a high sneak, just step by the hay pile and let them go through (There are two guards.)

Then. just take a right, around the corner, and head for the manhole exit. You will find yourself on a platform of land behind a house. Just hop down and you are free. If you do not get the option to activate the crumbling wall, you can also phase through the wall very easily using the wooden plate on the table.

Escaping without using secret passages is a lot harder. Unfortunately the steps are too complicated to mention, due to guards being everywhere, but there are a few basic things you need to have. Firstly, you need to have a good level of magic, and make sure you can cast Detect Life and Muffle (Invisibility is good too).

To escape, the basic route is to escape your jail cell, walk to the passageway directly ahead, follow the path up the steps, turn first left, down the steps, and the belongings chest will be on a table. Follow the path onwards and eventually you will reach the door into Castle Dour, and then Solitude.

You can also wait for the guard to stroll around and pickpocket the jail key to unlock all the cells of Maine or just your own. The key can also be used  to take your belongings from the chest rather than picking the lock.

Whiterun
Once you commit a crime in Whiterun and the guards catch you, you can choose to end up in the Dragonsreach Dungeon.

Once you are inside your cell, you are stripped of all your items except for one lockpick. There are two possible ways to escape from the prison. The first one is shorter but much riskier. When you're out of sight of any guards, pick the lock to the main door of your cell (an Adept Level Lock). Then you must reclaim your equipment.

You can find it in the evidence chest, but watch out as a guard patrols the area. Once you get your equipment, you must carefully escape through the main door, because there are several guards patrolling there as well.

The other way of escaping is a lot longer and safer, but it's still not that easy. In your cell there will be a dead bandit lying on the ground. The bandit will be lying on top of a sewer grate with a Novice Level Lock. Open it and you will fall into the sewers.

As you progress, you should see a set of stairs leading to a hole in the wall. Through the hole, you can pick the lock on the evidence and prisoner belongings chest to get your things back. Deeper into the dungeon you will see the exit into the guard barracks. Step through and you are free.

Note: Proceed with caution as the guards may become hostile to you after your jailbreak.

Another way is much more action worthy equip the spell sparks and wait for a guard to come by and unleash lightning, keep shooting sparks and then the guards will retaliate they will open the cell door and you can run for it

(Try to get your equipment first)

Windhelm
Escaping Windhelm prison is quite difficult, and a high sneak is recommended.

To breakout, the prisoner needs to pick the lock of your jail cell. There is only one exit, so head up the path and up the stairs. There will be a fork, so just head out of the keep.

Raven Rock (Dragonborn DLC)
Escaping the Bulwark prison is quite easy, as even low level thieves can escape without alerting the guards.

To escape, look under the firewood of the fireplace. Unlock the novice level grate and drop down. Run to the right and head to the edge of the walkway. Unlock the prisoner belongings chest to get your stuff and then drop down again. Continue through the sewers until you find the door to Coldcinder Cave. Enter the medium-sized cave (There are skeevers and a few netch here, which help for the quest to find Netch Jelly for the Raven Rock alchemist.) and walk out.

Dawnstar
The jail layout of Dawnstar is the same as Falkreath.

First, as with most cities, you will start in a cell with one lockpick. Be careful when picking the lock because once you succeed the guard will know and come over to your cell. You can also pickpocket the key off of the guard.

Note that in the back right corner of the cell there is the lockpicking skill book The Wolf Queen, Book I.

Also, a much better way is to shout at the wall. The guard will come over, telling you to stop and leave the door open. What's more, if you leave your cell the guards will NOT be hostile.

Once you exit out of the cell, turn left to find a desk and the evidence and belongings chests which contain your equipment. You can steal the key off the desk or lockpick the chests to get your belongings back.

The exit out of jail is right in front of your cell.

Falkreath
The jail layout of Falkreath is the same as Dawnstar.

First, as with most cities, you will start in a cell with one lockpick. Be careful when picking the lock because once you succeed the guard will know and come over to your cell. You can also pickpocket the key off of the guard.

A second, much better way is to shout at the wall. The guard will come over, telling you to stop and leave the door open. What's more, if you leave your cell the guards will NOT be hostile.

Once you exit out of the cell, turn left to find a desk and the evidence and belongings chests which contain your equipment. You can steal the key off the desk or lockpick the chests to get your belongings back.

The exit out of jail is right in front of your cell.

Morthal
The jail layout of Morthal is similar to Dawnstar and Falkreath.

As always, you start with one lockpick. You can either pick the lock or shout at the wall, the guard will come over and request you to stop, walking away without locking the door.

Be careful when opening the cell door as the guard will come over. Just hide in the opposite corner of the bed and he won't notice you. Proceed to either sneak or kill the guard.

Your belongings will be in a chest just a little front of the cell. You can walk out a little, then find a barrel with 3 extra lockpicks to help in picking the chest lock.

The exit is in front of the cell door, but BE CAREFUL. There are 4 guards on duty here, and escape is almost impossible unless you have high sneak or cast a spell.

You can also shout whirlwind sprint at the wall and go through it and spawn next to the door, but don't forget your items. This may not work every time. (tested only on Xbox 360)

Winterhold
The Chill is rather unique as you get to keep all of your stuff, even the stolen goods.

First off, after being arrested you are transported very far north, past Septimus Signus's Outpost. Next you'll find yourself in a small cage with one Frost Atronach acting as a guard. Kill it using Shouts if you are low level, or open the gate and battle it if you think you are ready, or use the spell Flames on it from inside the cage (it won't attack if you kill it in this way) Note: spells other than Flames, Sparks, Frostbite, Arniel's Convection, or Vampiric Drain will impact on the cage walls. (i.e. Concenctration Spells)

The cage itself is an adept lock so, before you turn yourself in, bring lockpicks. Outside are three other frost atronachs and there is a chance to see a Sabre Cat depending on your level.

To escape, just turn around and run up the small mountain onto an ore vein. The enemies will not get to you and will eventually give up, allowing you to fast travel away.

However, if the Dragonborn is not yet strong enough to fight Frost Atronachs, the simplest thing to do, since you have all your inventory intact, is to pick the lock and sprint out of the cave and into the ocean, where atronachs will not try to fight you.

Tips

 * If you plan to go in jail on purpose, you can make your escape easier even before you get arrested; get in the Guard Barracks and drop some lockpicks or anything you want before each (if you don't know which cell you will be put in) cell door.
 * As keys cannot be dropped once obtained, only stored (If the jail has something which you can storage items in, a key can be placed inside.) There is no need to try and get them before being placed in jail.
 * While in jail, if you still have the Skeleton Key obtained during the Thieves Guild Questline, (though it may not show up in your inventory) you will use that to pick the locks instead of normal lockpicks.
 * If you have the Lesser Power Secret Servant from the expansion, you can use him to smuggle any items into the cell, assuming it doesn't surpass his carry weight.

Bugs

 * If the player has a high bounty and is placed in the Solitude prison, the guards may be hostile even when the player is in their cell. This requires the player to sneak to the bedroll to serve their sentence, as to not stir the guards.
 * Sometimes when in the Whiterun prison, your belongings on the dead bandit will disappear. A way to avoid this is to place your belongings on the dead skeever or a barrel in the sewers to collect. Be cautious when using barrels to store your things, since they will reset to normal barrel contents after a certain period of time.
 * The Riften jail's escape route marked by a Thieves Guild Shadowmark is still bugged. A button next to the symbol will say "Activate Broken Shackle", and usually upon activation will force a wall to collapse in the back. For now, the chain that is usually there is not rendered, and the wall itself will not collapse.