Heat a large skillet over high heat. Add the olive oil.
Season one side of the chicken breasts with the salt and pepper. Place seasoned-side down on the skillet and sear over high heat for 4 minutes. Season the up-facing side. Flip over and cook for an additonal 4 minutes. If your chicken breasts are exceptionally thick, you can cover the skillet with a lid, turn heat to low, and let them finish cooking through for 10 minutes. Internal temperature needs to be 165°F, but I usually just measure done-ness with my eyes (make sure there isn't any pink left in thickest part).
Let the chicken rest for at least 10 minutes (this helps the juice stay in the chicken) then slice into 1/2 inch pieces.
Toss the chicken with the dressing, then assemble the wraps. Lay out a tortilla, line it with lettuce, then add the chicken salad, olives, and capers. Fold the tortilla lengthwise over the filling, tuck in the sides, and roll into a secure wrap. Repeat for each wrap.
Slice each wrap in half and enjoy! Or, if you are meal prepping, slice your wraps in half and store in an airtight container in the fridge for easy grab-and-go lunches.