Preheat the oven to 350°F.
Coat the peeled garlic cloves in oil, wrap in foil and roast for about 20 minutes, until caramelized.
Tear the bread into cubes and toss with oil, garlic, salt and pepper on a baking sheet. Roast for 13 minutes, until golden and crisp.
Pat the chicken breasts dry with paper towel, brush with olive oil and season both sides with salt and pepper. Arrange on a baking sheet and roast until cooked through, 15-20 minutes. Let the chicken rest for 5-10 minutes before slicing on the diagonal.
Add all of the Caesar dressing ingredients, including the roasted garlic, except the oil to a blender, food processor, or immersion blender. As the mixture is blending, slowly add the oil to emulsify. Season to taste.
In a large serving bowl, toss the kale with the caesar dressing, shredded parmesan and croutons. Divide between bowls and top with sliced chicken breasts.