Heat oil in a skillet over medium. Cut chicken into cubes and season with salt and pepper; add to skillet. Sauté until chicken has browned and is no longer pink inside. Remove from heat and cool.
Chop olives and mix with dressing and cooled chicken.
Fill tortillas with chicken and lettuce; wrap tightly and cut in half.
Serve with blueberries and cubed watermelon on the side.