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Is there a way to create a quick checkerboard pattern that can used to draw behind a shape? I can use the Rectangle Grid to make a normal grid to do this but when I create a checkerboard shape the draw behind option is grayed out. Polar Grid has an option to alternate ring color but I don't see one in Rectangle Grid. The only other way I can think of is to build the squares individually.

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It probably won't get much easier than using the included checkerboard fill pattern. In CC14 you can find it within the "Decorative Legacy" swatch. Use the scale tool to adjust the size as necessary.

Checkerboard pattern in Illustrator

Alternatively you could make your own pattern.

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