Heat a skillet over medium heat and add a drizzle of olive oil. Once hot, place the bacon strips in the skillet and cook for 2-4 minutes on each side, or until crispy. Remove the bacon, chop into bite-sized pieces, and set aside.

Season the chicken breast with kosher salt and cracked black pepper. In the same skillet, sear the chicken for 4 minutes on each side until browned. Transfer to a preheated oven at 400°F (200°C) and roast for an additional 9-12 minutes, until cooked through. Let rest before slicing.

Chop iceberg lettuce into bite-sized pieces. In a mixing bowl, combine chopped lettuce with diced chicken, crispy bacon, Caesar dressing, and grated Parmesan cheese. Toss until well-coated.

Lay tortilla flat on a clean surface. Spoon salad mixture into the center, fold sides inward, and roll tightly to create a wrap.

Toast the wrap seam-side down in the skillet over medium heat for 1-2 minutes until golden. Flip to toast the other side for another 1-2 minutes.