Start by chopping the cooked chicken, lettuce, and tomatoes. Grate the Parmesan cheese fresh and make sure the lettuce is washed and dried completely. A little moisture can make the wrap soggy, so dry greens are key.
In a large mixing bowl, combine the chicken, romaine, tomatoes, croutons, Parmesan, and a few cracks of black pepper. Add the Caesar dressing gradually and toss gently so everything gets evenly coated but not drenched.
Lay a tortilla flat on your surface. Spoon a generous amount of the chicken mixture along one side of the tortilla. Fold the sides in, then roll it up tightly like a burrito. Slice it in half diagonally for easier handling and a neat presentation. Repeat with the remaining tortillas.