Preheat oven to 375°F (190°C).
In a small mixing bowl, combine softened cream cheese, chopped spinach, dried cranberries, and minced garlic until homogeneous.
Butterfly the chicken breasts by slicing horizontally through the center, stopping 1/2 inch from the edge to create a pocket.
Season the interior and exterior of the chicken with salt, pepper, and paprika.
Distribute the cream cheese mixture evenly among the four chicken pockets and secure the openings with 2 toothpicks each.
Heat olive oil in a large oven-safe skillet over medium-high heat.
Place chicken in the skillet and sear for 3-4 minutes per side until a golden-brown crust forms.
Transfer the skillet to the oven and bake for 12-15 minutes or until the internal temperature reaches 165°F (74°C).
Remove from oven and allow the chicken to rest for 5 minutes before removing toothpicks and serving.