(Optional) Warm the tortillas if you prefer them pliable: microwave wrapped in a damp paper towel 10–15 seconds or heat in a dry skillet 10–20 seconds per side.
In a large bowl, combine the cooked chicken, chopped romaine lettuce, halved cherry tomatoes, shredded or shaved Parmesan, and Caesar dressing.
Toss the mixture until the ingredients are evenly coated with dressing. Season with salt and black pepper to taste.
Divide the chicken mixture evenly among the 4 large tortillas, placing each portion in the center of a tortilla and leaving a 1–2 inch border at the edges.
Sprinkle the crushed croutons over the top of each portion.
Fold the short sides of each tortilla in toward the filling, then roll each tortilla tightly from one long edge to the other to enclose the filling; secure with a toothpick if needed.
Slice each wrap in half and serve immediately, or wrap tightly in foil or parchment for an on-the-go meal.