Cook the penne pasta according to package instructions until al dente. Drain and set aside.

In a large skillet, heat the olive oil over medium heat. Add the chopped bacon and cook until crispy, about 5-7 minutes.

Once the bacon is crispy, remove it from the skillet and drain on paper towels, leaving the rendered fat in the skillet.

Add the diced chicken to the skillet and sauté for 3-4 minutes until heated through.

Pour in the heavy cream and ranch dressing, stirring to combine all ingredients.

Add in the cooked pasta, cherry tomatoes, and crispy bacon. Toss everything to combine, and allow it to heat through for about 2-3 minutes.

Stir in the cheddar cheese until melted and season with salt and pepper to taste.

Serve immediately and enjoy your creamy chicken bacon ranch pasta!