Preheat the oven to 400 degrees and grease a baking dish with nonstick cooking spray.
Stir together the cream cheese, half the garlic powder, half the dill, pickle relish, chopped pickle slices, and half the shredded cheese until well combined.
Place the chicken breasts on a flat surface and use a mallet to flatten and tenderize the meat.
Season one side of the chicken with the remaining garlic powder, remaining dill, salt and pepper.
Flip the chicken over and spread the cream cheese mixture in an even layer over the top.
Roll up the chicken breast over the cream cheese filling and use toothpicks to hold the chicken in place.
Heat the olive oil in a medium skillet over medium heat. When the skillet is hot, add the chicken pieces and sear each side for 2 to 3 minutes, until golden brown.
Transfer the chicken pieces to the baking dish and bake for 15 minutes, then remove the pan from the oven and top with remaining shredded cheese. Return the pan to the oven to bake for another 5 minutes, until the cheese is melted.