Preheat the Oven - Set the oven rack to the middle position and preheat to 400ºF (204ºC). Line a rimmed baking sheet with foil.
Make the Seasoning - In a small bowl, combine salt, paprika, garlic powder, onion powder, black pepper, and Italian seasoning.
Season the Chicken - Thoroughly dry each chicken breast with a paper towel. Evenly sprinkle both sides with the seasoning mixture.
Wrap with Bacon - Start at the wider end of the chicken. Gently stretch and wrap a piece of bacon around and down towards the middle. Slightly overlap the edges to secure it on the chicken. Use the second piece of bacon to finish wrapping down towards the tapered end. The seams should be beneath the breast to prevent unraveling. Repeat with the remaining pieces. Transfer to the foil-lined pan.
Glaze (optional) - Brush the surface of the bacon-wrapped chicken with maple syrup if using. Sprinkle with black pepper, if desired.
Roast - Cook until the internal temperature reaches between 160 to 165ºF (71 to 74ºC) on a meat thermometer, about 25 to 30 minutes, depending on the thickness. The bacon should be fully cooked. If desired, brush with the rendered bacon grease and maple syrup.
Serve - Transfer to a paper towel-lined plate to drain off any excess grease on the bottom. Allow the chicken to rest for 5 minutes before serving.
Notes
For a Crispier Surface: Broil on high after the chicken reaches an internal temperature of 160ºF (71ºC) until the surface is crisp, about 2 to 4 minutes.
Large Chicken Breasts: Three pieces of bacon may be needed for wrapping.
Storing: Cool completely and store in an airtight container for up to 5 days.
Reheating: Reheat in the microwave on high in 30-second intervals until hot. Alternatively, bake on a foil-lined sheet pan at 350ºF (177ºC) until warm.