Pat the chicken breasts dry with paper towels and place them in a large mixing bowl. Add olive oil, garlic powder, onion powder, Italian seasoning, salt, and black pepper. Toss thoroughly until every piece is evenly coated with seasoning.
Heat a large skillet over medium-high heat. Once hot, add the seasoned chicken and cook for approximately 6–8 minutes per side, depending on thickness, until golden brown and the internal temperature reaches 165°F (74°C).
Transfer the cooked chicken to a cutting board and allow it to rest for at least 10 minutes. This helps the juices redistribute and keeps the chicken moist.
While the chicken rests, prepare the Caesar dressing by combining Greek yogurt, grated Parmesan cheese, lemon juice, Dijon mustard, Worcestershire sauce, minced garlic, salt, and pepper in a bowl. Whisk until smooth and creamy.
Wash the romaine lettuce thoroughly and dry it completely. Chop into bite-sized pieces. Slice the cherry tomatoes in half and prepare any optional toppings.
Slice the rested chicken into thin strips or bite-sized pieces for easier wrapping and even distribution.
In a large bowl, combine the chopped romaine lettuce, sliced chicken, shaved Parmesan cheese, tomatoes, and prepared Caesar dressing. Toss gently until everything is lightly coated.
Lay one tortilla flat on a clean work surface. Add one-quarter of the chicken Caesar mixture to the center, keeping the filling compact.
Fold both sides of the tortilla inward over the filling. Starting from the bottom, roll tightly until a secure wrap forms.
Repeat the process with the remaining tortillas and filling.
For meal prep, wrap each finished wrap individually in parchment paper or foil and place in airtight containers.
Refrigerate until ready to serve. Enjoy cold or slightly warmed, depending on your preference.