Cook the penne pasta according to package instructions until al dente. Drain and set aside, reserving 1/2 cup of pasta water.
In a large skillet, heat olive oil over medium heat. Add minced garlic and red pepper flakes, sautéing for about 1 minute until fragrant.
Add the halved cherry tomatoes to the skillet and cook for 5-7 minutes until they start to soften. Stir in the cooked pasta and fresh basil, mixing well. If the pasta seems dry, add a little reserved pasta water to reach the desired consistency. Season with salt and pepper to taste.
While the pasta is cooking, prepare the grilled chicken. In a small bowl, whisk together balsamic vinegar, honey, dried oregano, garlic powder, and black pepper.
Preheat a grill or grill pan over medium-high heat. Brush the chicken breasts with the balsamic mixture and grill for 6-7 minutes on each side, or until the chicken is cooked through and has nice grill marks.
Remove the chicken from the grill and let it rest for a few minutes before slicing.
Serve the pasta topped with sliced grilled chicken and an extra drizzle of the balsamic mixture if desired.