Jail Break (Skyrim)

This is a quick guide to escaping out of jail/prison in all the cities of Skyrim. This guide will be telling you 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 your time. (However there is a bug in which you can trap yourself in Cidhna Mine forever by hitting the ore with a pickaxe, you can deplete the silver veins and since the ore doesn't reset after a certain amount of time you will never be able to get the option to serve your time. See the Cidhna Mine article for a fix to this bug.)

Riften
You start off in what looks more like an ill-treated hotel room than a cell. To your right there is a desk with a lockpick hidden amongst the food. Behind you is the bed, and to your left is a dresser and a bucket. If you notice carefully there is a shadowmark on one of the pillars, hinting a secret escape route.

Firstly pick the lock of your jail cell or pickpocket it off the guard who will be standing next to you when you start. Sneak towards the passageway to your left, then enter a door on the left hand side (not in front). Turn left, enter another door, and you will find your belongings chest in the top right hand corner.

Exit out the same way but turn right and go through the door you might have 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 an adept lock. You can also loot the key off the guards one 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.

The 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.

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 search for 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 chest and get your things back. Deeper into the dungeon you will see the exit into the guard barracks. Step through and you are free.

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

First of, as with all jails, you need to pick the lock of your jail cell. There is only one exit, so head up the path and up the stairs. You will come to a fork at the top of the stairs, choose the right path and keep going.

The prisoner belongings chest will be right beside you, in the corner, once you come out of the path and into a big guard barracks room. Just head through it, keep following the only path and eventually you will come to a door to the Palace of the Kings.

At this point, the guards will not try to arrest you, so just head out of the keep's main doors on your left.

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.

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 lots of 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 third, 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 lots of 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 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, arniels convection, or vampiric drain will impact on the cage walls.

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.
 * If you have high Pickpocketing skill, you can steal it from the guards patrolling around the prison, then drop the key before the cell door if you will be jailed later on(you must know which cell you will be put in, if you want to do this).

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.
 * Sometime in Whiterun prison your belongings on the dead bandit will disappear. A way to avoid this is to place your belonings on the dead skeever or a barrel in the sewers to collect. This does not work. If you store items in the barrels, they will eventually be replaced by generic barell items (e.g. Apples)