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Sprinkle chicken with Italian seasoning, salt and pepper.
Heat oil in a small skillet over medium-high heat. Add the chicken; cook until golden on one side, 2 to 3 minutes. Flip the chicken and reduce the heat to medium-low; cover and cook until an instant-read thermometer inserted in the thickest portion registers 165°F, 7 to 10 minutes more. Transfer to a cutting board and let rest for 5 minutes.
Cut 1 chicken breast horizontally, from the thickest edge nearly through to the opposite side. Open up the breast and spread ¼ tablespoon pesto on both cut sides. Fill with 2 tomato slices and 2 mozzarella slices. Drizzle with ½ teaspoon balsamic glaze and garnish with half of the basil. Close the breast over the filling. Repeat with the remaining chicken breast and filling.