Heat the olive oil in a large skillet over medium-high heat. Season the chicken thighs with salt and pepper on both sides.
Once the oil is hot, add the chicken thighs skin side down and sear for about 5-7 minutes until the skin is golden brown. Flip the chicken and cook for another 5 minutes.
Sprinkle the ranch seasoning mix evenly over the chicken thighs.
Add the cream cheese and chicken broth to the skillet, stirring gently to combine. The mixture will begin to melt and create a creamy sauce.
Reduce the heat to medium-low, cover the skillet, and let it simmer for about 15-20 minutes, or until the chicken is cooked through and reaches an internal temperature of 165°F (75°C).
Remove the lid and sprinkle the shredded cheddar cheese and bacon bits over the top of the chicken. Cover again for a few minutes until the cheese is melted and bubbly.