Season chicken thighs with 1 tablespoon olive oil, salt, garlic powder, black pepper, and oregano, tossing to coat. Let sit for 10 minutes.

Heat 1 tablespoon oil in a Dutch oven or deep pot over medium heat. Lay chicken in an even layer and sear until browned on both sides. You may have to sear the chicken in batches if they don't fit all at once. Remove chicken and set aside.

In the same pot, melt 1 tablespoon butter. Add chopped onion and saute until softened, about 4-5 minutes. Add garlic cloves and red chili flakes and saute for another minute. Add orzo and toast for 1 minute, stirring to coat.

Add tomato paste, Italian seasoning, balsamic vinegar, cherry tomatoes, and chicken stock. Add chicken back to the pot, nestling them in the orzo. Bring to a boil, cover the pot, and reduce heat to low. Continue to simmer until orzo is cooked and tender, about 15 minutes.

Remove lid and top with grated parmesan and fresh basil. Serve immediately.