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I'm starting an Ork army and in my research it seems that they often have checker boards painted on them. Is this done free hand? is there a better way?

First paint the brighter colour, then make a grid with the darker colour and then fill in the squares. Doesn't have to be super neat with orks.

Freehand? Generally, yes. You can also use transfers to get a very neat design, but they work best on regular surfaces - flats and simple curves without much texture (rivets, etc.). You can also mask and spray them, but the labor involved in cutting and placing a mask generally only nets you a time savings for large patterns, like those found on vehicles (e.g. Dakkajet nose/wings).

Personally, I like to use a Micron pen (Sakura Pigma is my brand of choice). Some folks use one to lay out their grid but fill the squares with paint. I do the whole thing with the markers, as I'm generally doing very small patterns that lack internal highlights (once sealed, the ink looks no different than a dark black paint, so it's purely a matter of convenience).

I also don't prescribe to the "it's Orks, so go ahead and be sloppy" doctrine, as many here do, which means I want the precision a Micron pen affords. To me, a loose or crooked pattern reflects poorly on the actual painter, not the assumed Ork grot painter, and simply doesn't look as good. Of course, some folks have sufficient brush control to use a brush and paint for the whole process with equally clean results. I wasn't one (due in no small part to having naught but crappy brushes with crude points) when I started applying checks and dags, and I've simply stuck with the same method.

Gargantuan is entirely right, though, that you should start with your lighter color. Makes things much easier on you.

Your wish is my command as I did a tutorial on my blog.

http://uniteallaction.blogspot.co.uk/2011/06/tutoria-how-to-paint-black-and-white.html