Season the chicken breast with kosher salt and cracked black pepper. In a skillet over medium heat, add 1 tablespoon of olive oil and cook the chicken for about 5-7 minutes on each side until fully cooked.

In another skillet, add another tablespoon of olive oil if needed and cook the bacon over medium heat until crispy and golden brown, about 4-5 minutes. Transfer to a paper towel-lined plate to drain.

Chop the iceberg lettuce into bite-sized pieces after rinsing and drying it.

Lay the tortilla flat, spread 2 tablespoons of Caesar dressing in the middle, and layer on chopped lettuce, diced chicken, and crumbled bacon.

Sprinkle ¼ cup of freshly grated Parmesan cheese over the top of the ingredients.

Roll the tortilla tightly, folding in the sides first, then rolling from one end to the other.

Slice the wrap in half and serve immediately.