Preheat your oven to 400°F and line a baking sheet with parchment paper. Toss the cubed squash with one tablespoon of olive oil, salt, and pepper until evenly coated. Spread it in a single layer and roast for 25 to 30 minutes, flipping halfway through for even browning.
While the squash roasts, bring the chicken broth to a boil in a saucepan. Stir in the rice, cover, and reduce the heat to low. Let it simmer for about 15 to 18 minutes, or until the liquid is absorbed and the rice is tender.
Pat the chicken breasts dry with a paper towel so the seasoning sticks better. Rub them with the remaining olive oil, minced garlic, rosemary, thyme, paprika, salt, and pepper. Let them sit for a few minutes so the flavors soak in before cooking.
Heat a large skillet over medium-high heat and add the seasoned chicken. Cook for about 6 to 7 minutes per side, until golden brown and cooked through to 165°F internally. Let the chicken rest for a few minutes before slicing so the juices redistribute.
Fluff the cooked rice with a fork and stir in the grated parmesan and chopped parsley. Plate the rice, top with roasted squash, and slice the chicken over everything. Finish with an extra sprinkle of parsley for a fresh, colorful presentation.