Which side is best to castle on?

Hi guys. Obviously, getting in a position where you can castle is great, but what if you could castle both ways? King side or Queen side- which is preferable? Does it depend on the situation, is it purely preference or does it not matter at all?

I would appreciate your thoughts.

Many thanks!

It depends entirely on the position at hand.

As with everything in chess, there are exceptions and position to take into account: usually I find castling short/kingside (O-O) to be safer and long/Queenside (O-O-O) to be more aggressive.

To better evaluate what makes each as I described, let us compare from the White side (The principles of course are the same for Black, but if I choose one side I can describe via the squares). If the White Rooks are on a1 and h1 (and we can castle) with the White King on e1 look what happens ...

castling short gets our King (on g1) nicely protected with our Rook on the f-file. The King guards the h2 pawn (if still there of course) and our Rook is on the third file from the right (f-file).

Castling long gets our King (on c1) safer than uncastled, but the a2 square (and pawn if still there) is not protected by the King. More often then not the King will use up another move to guard this (in this example, moving to b1). The Rook in this case (on d1) is on the fourth file from the left (d-file).

It is nice to have a Rook developed towards the center since these clumsy pieces sometimes get stuck in the corners (which castling long does better for Rooks), but the King is also nicer tucked safely away (which castling short does better for King safety).

When solving which move is better in chess (like which way to castle), I like to see what each move does better or worse than the other. Sometimes one decision versus another frees an important square, other times one move developes better than the other, sometimes one move keeps more options (than committing yourself to something). A strong player tends to notice these subtle differences, and as any chess player knows: a little difference can be a difference that decides the game!  

To summarize, O-O is usually safer and O-O-O is usually more aggressive. Obviously though, this is purely excluding other factors to evaluate on the board (but there always seems to be more to evaluate).

I always try to castle on my kingside, and I try to use my kingside bishop and knight as guards, and as defense. I find castling on the queen side tends to give problems, although depending on the situation, you may have no choice but to go ahead and castle on the queen side to avoid danger. I don't know what your key openings are when playing chess. I've been using Scotch and the Italian opening, and both openings allow me quick castling, and also gives me an advantage at getting my pieces quickly established. Just evaluate each move as best as possible, and you should do fine! 

Correct. But it depends on what opening you use, and where your pieces are located on the board. Personally, I stopped castling on the queen side years ago, as I found my opponent always found a way to sneak his knight in there, and catch me in fork that I did not notice. Besides, grand masters always castle on the king side. If they do it, it has to be doing something right. 

Of course it depends on position)

Hi guys. Obviously, getting in a position where you can get out of the middle of a highway is great, but what if you could get out both ways? Left side or right side- which is preferable? Does it depend on where the next car is coming from, is it purely preference or does it not matter at all?

I would appreciate your thoughts.

Many thanks!

Simplified: Castle on the safest side. And I'm done here. 

+1

What about here? You are pretty safe either side and, although this situation is unlikely, you have a clear choice...

Thoughts..?

on rooks side? maybe?

In post #12, I'd favor O-O in this symmetrical position. Castling short (Kingside) should be the "go-to -thought" as castling the other way has is not without its risks. My earlier post (#4) details a bit more into why. 

In the position in post #12, I'd think about castling short (castling long has its points to though [in this example, the Rook onto the d-file comes to mind]).

You can't say for sure since it always depends on the position, but for most players most of the time, 0-0 is preferable. The King is more secure without wasting another move (Kc1-b1 is often needed when you 0-0-0), and you can do it wicker & more in the natural early flow of developing. For beginning or improving players, it's best to stick to 0-0 unless early play makes it unsafe for some reason.

You should castle on the opposite side when at least one of the following factors is true:

1. When you are up in development and your opponent has already castled, you should consider castling in the opposite side. That way you will have a clear game plan and will also be able to capitalize on your development advantage.
2. When you have a damaged pawn structure (doubled paws, missing pawns, far advanced pawns, etc.) on one of the sides you should consider castling on the other side.
3. When opponent’s pieces are especially active on one side of the board, it is usually best to castle on the opposite side.
4. If you want to complicate the game you may consider this option. That may be true if you must play for a win due to a tournament situation, when the draw is not enough. Also that maybe done when you're playing against a stronger opponent, who is much better in simple/technical positions. That maybe your best bet.

You should not castle on the opposite sides when at least one of the following factors in true:

1. When you are behind in development and you need extra time to develop your pieces, it is usually not a good idea to give your opponent a straight forward way of launching an attack.
2. When the opponent’s pawns are advanced towards the side you’re about to castle, it is not a good idea to castle there (especially if the opponent’s king is castled on the opposite side). It will just give him a positional edge in the attack.
3. When there are open/semi-open files in-front of the side you’re about to castle, you should probably reconsider your decision to castle there (especially if your opponent has castled on the other side). That will give him more attacking possibilities, such as rook lifts, various sacrifices, doubling of pieces on the file, etc.
4. If you playing against a weaker opponent you may want to avoid castling opposite sides, in order to avoid sharp game and keep everything under control.

Note: These are general rules, not laws, meaning that there are always exceptions to them. When you’re making a decision what side to castle you should always take your time and evaluate all “pros” and “cons” and base your decision upon your own analysis. This is a very important decision. It pretty much dictates which way the game will continue. Take your time and think twice.

If your name is Fischer, the year is 1958, your opponent is Larsen, and he is playing the dragon... then castle queen side and sac the exchange.

I try and wait until my opponent castles then I usually castle opposite my opponent, I believe this provides ample protection and allows me the opportunity to attack and end the game. Knowing that most people castle on the short side gives me a heads up and i'm already planning my attack on that side in advance.

king side

Depends on the game, obviously, read the board to find the safest side to castle. Sometimes the better option is not to castle at all and attack at full force or protect the king in the central squares.

Saying that, I'm not an expert.

The kingside is on the right side or on the left side and the queenside is on the left side or on the right side, depending on what side you are playing on.