In a large bowl, toss the chicken with the olive oil, Worcestershire sauce, garlic powder, onion powder, paprika, smoked paprika, salt, and pepper until evenly coated.
Heat a large skillet over medium-high heat. Add the chicken and cook for 6 to 8 minutes, stirring occasionally, until browned and cooked through. Transfer to a plate and let rest for a few minutes.
While the chicken rests, whisk together the mayonnaise, Dijon mustard, honey, vinegar, lemon juice, garlic powder, salt, and pepper in a small bowl until smooth and creamy.
Warm the tortillas for a few seconds in the microwave or in a dry skillet until soft and flexible.
Spread about 2 tablespoons of honey mustard sauce down the center of each tortilla.
Divide the warm chicken evenly among the tortillas and immediately sprinkle the cheddar cheese over the top so it softens slightly.
Add the romaine lettuce, diced tomato, red onion, and dill pickle chips if using.
Place 2 slices of crispy bacon on each wrap and drizzle with an additional spoonful of honey mustard sauce.
Fold in the sides and roll tightly.
Place the wraps seam-side down in a dry skillet over medium heat and toast for 1 to 2 minutes per side until lightly golden and crisp.
Let the wraps rest for 1 minute before slicing in half and serving.