Whisk together olive oil, fresh lemon juice, minced garlic, dried oregano, salt, and pepper to prepare the Greek dressing. Adjust acidity by tasting for a balanced, bright flavor.
Coat boneless chicken breasts with olive oil, lemon juice, garlic, oregano, salt, and pepper. Grill or pan-sear over medium heat until golden and cooked through. Let rest before slicing to retain juiciness.
Dice tomatoes, peel and slice cucumber, and thinly slice red onion. Soak onion in cold water briefly to mellow sharpness. Drain and pat dry all vegetables to prevent sogginess.
Toss chicken slices with prepared vegetables, Kalamata olives, and crumbled feta in a large mixing bowl. Drizzle generously with Greek dressing and gently mix to combine while keeping textures distinct.
Lightly toast pita bread on a grill or skillet to add a slight crunch and smoky aroma. Warm pita increases pliability, making it easier to stuff without tearing.
Stuff each pita pocket generously with the salad mixture or serve the salad bowl-style alongside pita wedges. Garnish with fresh herbs like parsley or dill for added color and aroma. Enjoy!