Preheat your oven to 400ºF. Spread the butternut squash on a baking sheet, toss with 1.5 tablespoons of olive oil, salt, and pepper, then roast for 25-30 minutes until tender.
While the squash roasts, prepare the chicken. Pound the chicken breasts until they're about ½-inch thick. Dip each breast in egg, then coat in a mixture of panko and parmesan.
Heat olive oil in a skillet over medium-high heat. Cook the chicken for 2-3 minutes on each side until golden brown and cooked through.
Massage kale with olive oil until softened. Add chicken, squash, radicchio, and shaved parmesan to the bowl.
Slice the chicken, add it to the bowl, and toss everything with caesar dressing until coated.