Heat 1 1/2 Tbsp olive oil in a skillet over medium-high heat.
Season both sides of chicken evenly with salt and pepper and Italian seasoning.
Cook chicken in skillet about 5 minutes per side, or until center registers 165 degrees. Remove chicken from skillet cover with foil to keep warm.
While chicken is cooking, in medium non-stick skillet cook bacon over medium-high heat, tossing occasionally until cooked through, about 6 - 8 minutes, drain on a plate lined with paper towels.
Heat remaining 1 1/2 Tbsp olive oil in a skillet that was used to cook chicken over medium heat.
Add asparagus, season lightly with salt and cook, tossing occasionally until tender-crisp, about 4 minutes. Add garlic and saute 30 seconds longer.
While asparagus is cooking, in a small saucepan melt butter over medium heat. Add in flour and cook and stir constantly 1 minute.
Pour in milk, season with salt, and bring mixture to a simmer, stirring frequently. Remove from heat and stir in parmesan, whisking well until melted.
Plate chicken and asparagus, drizzle over the cheese sauce, and sprinkle with bacon and pepper. Serve warm.