Prep the Dressing and Croutons: If making homemade Caesar dressing and croutons, prepare both first and set aside at room temperature while you work on the rest of the recipe.
Boil the Pasta: Cook the penne in a large pot of heavily salted boiling water until al dente according to package directions. Drain immediately and rinse under cold running water until the pasta is fully cool. Let it drain thoroughly in the colander before using.
Crisp the Bacon: Cut the bacon into small pieces using kitchen shears and cook in a dry pan over medium-high heat, stirring occasionally, until deeply golden and properly crispy, about 8 to 10 minutes. Transfer to a paper towel-lined plate and leave all the rendered fat in the pan.
Pan-Fry the Chicken: Season the chicken pieces on both sides with garlic powder, salt, and black pepper. Return the pan with the bacon fat to medium-high heat. Once the fat is shimmering, lay the chicken flat in the pan and cook for about 5 minutes per side until deeply golden outside and fully cooked through. Transfer to a plate, rest for 5 minutes, then slice into strips.
Assemble the Salad: Add the cooled drained pasta and chopped romaine to your largest salad bowl. Lay the sliced chicken on top, scatter the crispy bacon bits across, add the croutons, then pour the Caesar dressing over everything. Toss gently from the bottom up until the dressing coats every piece.
Finish and Serve: Top with freshly grated parmesan and a small squeeze of fresh lemon juice if using. Taste and adjust dressing or seasoning as needed. Add the croutons right before serving so they stay crunchy. Serve immediately or see the make-ahead note below.