Preheat oven to 350 degrees F.
Toss cherry tomatoes with olive oil and balsamic vinegar. Season with salt and pepper. Lay tomatoes on a baking sheet and roast for 30-35 minutes or until softened and blistered. Remove from the oven and set aside.
Prepare parmesan chicken. Combine parmesan with Italian seasoning, garlic powder, salt, pepper, and red pepper flakes in a large bowl. Press chicken into parmesan seasoning mix on both sides to create a parmesan crust.
Heat 1 tablespoon in a large saute pan over medium heat. Cook chicken until golden brown on both sides and the juices run clear, about 7-8 minutes. Remove from heat and keep warm.
Melt 2 tablespoons butter in a large saute pan over medium heat. Add corn and saute until lightly charred. Remove from heat. Combine 1 ½ cups cooked corn with basil, garlic, ½ cup parmesan, and ¼ cup extra virgin olive oil in a food processor or blender. Puree until smooth and season with salt and pepper.
Cook penne pasta according to directions on package until al dente. Drain, reserving 1 ½ cups of the pasta water.
Reheat remaining cooked corn over medium heat. Add cooked pasta, corn pesto, remaining ½ cup grated parmesan, and 1 cup reserved pasta water. Stir until well coated and season with salt and pepper. If the pesto is too thick, add additional pasta water as needed. Add roasted cherry tomatoes, gently tossing to combine.
Slice chicken and portion pasta into plates, topping pasta with sliced chicken. Sprinkle freshly cracked black pepper and finish with extra parmesan if desired. Serve immediately.