In a medium bowl, coat chicken with 1/3 cup Caesar dressing. Making sure all of the chicken breasts are fully covered in the dressing. Cover the bowl with plastic wrap and let it sit on the counter for 20 minutes (but no longer) or refrigerate up to overnight. 

Meanwhile, prep the lettuce. Rinse and dry. Chop off both ends and the rib part of the lettuce. Cut into squares.

Once the chicken is done marinating, heat a medium sized pan over medium/high heat (I used a grilling pan). Add olive oil and chicken to the pan. Cook chicken for 5 to 6 minutes. Flip the chicken over and cook for another 5 to 6 minutes until fully cooked through. Remove from pan and let cool for  8 to 10 minutes before slicing.

Assemble lettuce, croutons, parmesan, remaining Caesar dressing, and chicken. Add more dressing as needed.