Heat 1 tablespoon of vegetable oil in a skillet over medium-high heat. Add bacon strips and cook for 2-4 minutes on each side until golden brown and crispy. Drain on paper towels and chop into bite-sized pieces.

Preheat your oven to 400°F (200°C). Season chicken breasts with kosher salt and cracked black pepper. Sear chicken for 4 minutes in an oven-safe skillet. Flip and transfer to oven, roasting for 9-12 minutes until internal temperature reaches 165°F (75°C). Let rest before slicing.

Chop iceberg lettuce into bite-sized pieces and place in a medium mixing bowl. Add sliced chicken, chopped bacon, Caesar dressing, and Parmesan cheese. Toss until well-coated.

Lay a tortilla flat and spoon the salad mixture down the center. Fold in the sides and roll tightly from the bottom to the top.

Heat a skillet over medium heat with a splash of olive oil. Toast the assembled wrap seam-side down for 1-2 minutes until golden and crisp. Flip and toast the other side for an additional 1-2 minutes.