Start by patting your chicken thighs dry with a paper towel. Season generously with salt and pepper on both sides. Heat 2 tablespoons of olive oil in a large skillet over medium-high heat. Place the chicken thighs skin-side down in the hot oil. Sear them for about 4-5 minutes per side until they are golden brown and crisp. Don’t worry if they’re not fully cooked yet; you’ll return them to the pan later. Remove the chicken from the skillet and set it aside.
Add the remaining olive oil to the skillet. Toss in your diced onion and sauté over medium heat until it begins to soften, about 2-3 minutes. Stir in the orzo and toast it lightly, which will bring out its nutty flavor. After 3-4 minutes, add the minced garlic and cook for another minute, being careful not to burn it.
Pour in the chicken broth while scraping up any brown bits from the bottom of the skillet using a wooden spoon. This step adds lots of flavor to the dish. Bring the mixture to a gentle boil, then nestle the chicken thighs back into the skillet. Reduce the heat to medium-low and cover the skillet. Simmer for 8 minutes.
Uncover the skillet and scatter the broccoli florets over the chicken and orzo. Replace the lid and continue cooking for another 12 minutes. This allows the broccoli to steam perfectly. By the end of this step, the chicken should reach an internal temperature of 165°F, and the broccoli will be tender.
Carefully remove the chicken thighs from the skillet and set them aside. Stir the shredded cheddar into the orzo and steamed broccoli until the cheese melts and the mixture is creamy. Taste and adjust seasoning if needed, then serve immediately.