Pat the chicken breasts dry with paper towels. Season generously on all sides with kosher salt and black pepper.

Heat the olive oil in a heavy skillet over medium-high heat. Sear the chicken for 5-6 minutes per side until a deep golden-brown crust forms and the internal temperature reaches 165°F (74°C).

Transfer the chicken to a cutting board, let it rest for 5 minutes, then cut into thick slices.

In a large mixing bowl, combine the chopped romaine, shaved parmesan, and lightly crushed rustic croutons. Drizzle with the Caesar dressing and toss aggressively until fully coated.

Warm the tortillas slightly. Spoon the dressed salad onto the lower-middle section of each tortilla. Top with the sliced golden-brown chicken.

Fold the left and right sides of the tortilla inward, then roll tightly from the bottom up to create securely packed layers.

Place the assembled wraps seam-side down in a dry skillet over medium heat. Toast for 1-2 minutes per side until lightly golden. Halve and serve.