1. Preheat your oven to 400°F (200°C).
2. Butterfly the chicken breasts by slicing them horizontally through the middle, but not all the way through. Open the chicken breasts like a book.
3. Season the inside of the chicken breasts with salt, pepper, minced garlic, and dried Italian seasoning.
4. Place 4-5 asparagus spears on one side of each chicken breast, parallel to the short end. Fold the other side of the chicken breast over the asparagus to create a pocket. Use toothpicks to secure the chicken if necessary.
5. Heat some olive oil in an oven-safe skillet over medium-high heat. Once the oil is hot, add the stuffed chicken breasts, seam side down, and cook for about 3-4 minutes until golden brown.
6. Flip the chicken breasts gently using tongs or a spatula, and transfer the skillet to the preheated oven.
7. Bake for about 15-20 minutes, or until the chicken is cooked through and reaches an internal temperature of 165°F (74°C).
8. Remove the skillet from the oven, and allow the chicken to rest for a few minutes before serving.
9. Carefully remove the toothpicks from the chicken breasts, and slice them crosswise into medallions.
10. Serve the asparagus stuffed chicken with your favorite side dishes, such as roasted potatoes, steamed vegetables, or a fresh salad.
Enjoy your delicious asparagus stuffed chicken!