Preheat your oven to 400°F (200°C).

Take one of the flattened chicken breasts and season it lightly with salt and pepper. Spread a tablespoon of pesto over the surface of the chicken. Carefully wrap the chicken breast with a slice of bacon, securing the roll with a toothpick. Place the bacon-wrapped chicken into a 9x9-inch baking dish.

Repeat the process with the remaining chicken breasts, ensuring they're all arranged snugly in the dish. Drizzle the vegetable oil evenly over the chicken rolls.

Bake the chicken in the preheated oven for about 30 minutes or until the bacon becomes crispy and the chicken is cooked through. To check doneness, insert an instant-read thermometer into the center of a roll; it should reach at least 160°F (70°C).