I have been traveling Skyrim through many saves, and finally am attempting a person who has 100 in every skill as well as has every perk. I've been working a while on lockpicking, picking any locks I can, though it is so slow.

It took me 3 Master chests to barely level from 72 to 73. Now I know there was the option of trainer in the Thieves guild, which I only did from 35 to 51... once fifty was reached even my Lv. 100 pickpocket, all perks, with armor with enchants for it I only had about a 50% chance to succeed. Besides that I was level 132, so I had to wait a long while before another 5 levels of tutoring. I saw some boring method of sitting at a chest, and letting your lockpicks break, giving you that little bit of xp every time, but from my current level I am sure that'd take well over 1000 picks. I have about 800, but have no good ways of getting a lot.

Anyone know of a good way to level it up? I am sure someone has tried to get 100 before.

Travel around to the different cities. At night time, break into every house you can.

I find it quite easy to level Lockpicking this way.
Be sure to have the Thief Stone, to get the bonus.

I'll try, but there are only so many buildings. I broke into every building in Whiterun, and every lockbox and chest as well. I only managed to level up twice, most of that was the Master lock for Acadia's lockbox and the several Expert locks from the companions weapon cases.

I just go to where I remember a Master locked chest is, and fail picking it over and over again while I do something else.

Boring, but considering the... odd decision Bethesda made so that you don't get experience for picking locks you've unlocked in the past (a decision that means it's really not a good idea to Legendary Lockpicking), it's really one of the few workarounds.

Edit: As for procuring lockpicks: Khajiit traders and Thieves Guild fences are your best bets.

On my thief character, I always buy lockpicks from Tonilia from the Thieves Guild, or any other fence, because they normally sell +15 lockpicks at a time for me at-least. Lockpicking can take some time to level up for sure. Just remember to NOT get the Wax Key perk, save it for last, since it will make you not able to level up your lockpicking skill on certain chests.

Alright, sounds like I am going to either have to find a ton of doors and chests to unlock, or to do the boring somewhat exploitish way... then again it isn't the first exploit I used on this save... so I guess I can't say it is a clean run.

It just takes a long time. Just play at your normal place and you'll get it to 100 eventually...in the 5th era...

-sigh- 650 lockpicks and almost an hour later... I find myself only up eleven levels.

I am 16 from 100... I can assume I'll need some where around 1000 more picks. Now the thieves guild person I believe sells 20-30 at a time so thats what? somewhere around 40 visits... averaging it to 25 per time. I'll just be glad to have unbreakable when this is all done... never need more than a single pick again. Not like I usually use more than 10 on a Master like... I can usually do it in about 2 or 3

EDIT: To my dismay, she does not die... so no kill load trick... guess i go to Khajiits

I find lock picking good on Skyrim. I used to hate the old way on Morrowind where you had to flick up the chambers. It felt like it took forever. At least this way is quicker.

All of the other fences you get from the Thieves guild quests have plenty of lockpicks too.

I'll stick to Khajiits. I know I can kill them, and know where to find them.

...Um...

If you don't mind me asking, why do you want to kill the Khajiit, or anyone else for that matter, for lockpicks?

Thief Stone, equip Aetherial Crown, then move to the Lover Stone. Go to sleep, until you get the well rested bonus.
This allows your lock picking to level 1.55x faster.

If you want to reach 100 I've always found it best to pay a trainer for the higher levels.

They will only train up to 90 anyway, it's something to do with all the money and it saves on grind.

I really enjoy lock-picking. But then I am a big fan of Thief and Thief II*.

Bethesda made a challenging in-game here. But like all skills - practice makes perfect.

Training as suggested in a previous post is a good idea. As are the practice chests found in the Thieves Guild.

A bundle of failed attempts on an Expert lock will soon get your stats moving.

* I almost expected Belethor (Stephen Russell) to chime in "Well that's the lost city Huh? Well it's not lost anymore" at some random event/easter egg.

Wait, why would you want to raise Lockpicking? You can open any lock with no skills whatsoever.

Words of wisdom here. Don't torture yourself, or those poor khajiit!

Umm...kill the khajiit for free lockpicks? Nah, I like these guys too much to kill them -and their moon sugar* too

*Moon Sugar: Essential ingredient for Elsweyr Fondue, if you're into that kind of thing.

Tonilia in the Thieves Guild sells 25-30 each time, just from selling my alchemy leveling potions and banish daggers (note that Im guild master so I can sell more at a time) I have over 700 lockpicks

I hated that in Oblivion too, until I got the Skeleton Key. I just mashed the 'square' button on my controller (which is the force lock button) until the lock opened; best of all, I got experience from that .

LPing is one of those skills that is tricky to power level, but I have it legendaried and I am I think at 63 now... just unlocking whatever I find.

My original character power leveled it by just buying a ton of picks(like 1,000) and repeatedly breaking them trying to unlock a master lock while I slept. Woke up with 100 skill.

Gather as many lock picks as you can, go to a master lock, keep breaking the lock picks over and over again and your lock picking will go up. It's quite easy to do if you have enough lock picks.

The buy, save, kill, reload, repeat thing.

Restores inventory.

Unfortunately upon further going, The whiterun Khajiit trader is another essential... I killed the Dawnstar Khajiits... I am ill fortuned it seems.

As a last resort, I will go that way, though I'd rather not wait a couple days for the restock.

Yea, I was using the trainer... but at level 175, It takes a VERY long time to get another level up, unless I do my quick levels trick... which I want to start limiting on (Illusion Legendary... Harmony levels it up quite fast) Ofcourse now I grinded my way to Lv 84... and leveled up recently... can train it to 89 I suppose... grind the last 11 with some Lockpicks from trades I accumulate...

I do not have any DLCs (yet)

Thanks for the help. I am sure I will have Lv 100 within a couple hours now.

EDIT: I just learned that even downing the Khajiit (though he lives) resets inventory upon load. So no Khajiits will killed in the process of this goal... only injured.

Lockpicking being difficult to level is news to me.