Bring a large pot of salted water to a boil. Cook penne until al dente. Drain and set aside.
Heat olive oil in a large skillet over medium heat. Cook chicken until golden and fully cooked. Remove and cut into bite-sized pieces.
In the same skillet, lower heat and add cream cheese. Stir until melted and smooth.
Add ranch seasoning and milk or broth. Stir until a creamy sauce forms.
Add cooked pasta, chicken, and bacon to the skillet. Toss to coat evenly.
Stir in shredded cheddar cheese until melted and creamy.
Season with black pepper to taste. Serve hot.