I would like to highlight my hair which is black. Do I need to bleach if the color I would like to achieve is a chocolate brown or caramel brown?

Have you dyed your hair before? It depends on how well your hair takes to color. I have had black hair and gotten it light without bleaching, but if your hair is more stubborn to color, you may need bleach.

I would try getting a bottle of light blonde dye and seeing if there is any change. If you dyed your hair to get it black, take a few strands and dye the bottom first. When hair is processed, the roots will change because its new growth.. the ends will be more stubborn.

If your hair has never been dyed it doesn't matter.

I would try that before bleach.

If your hair has been dyed, you won't be successful with anything but bleaching. If your hair is "virgin" (never been colored), you might be able to use a lighter hair color to get it to chocolate or caramel. Otherwise, use bleach.