Pat the chicken thighs dry with paper towels to ensure a good sear. Season both sides generously with salt, black pepper, and dried oregano. This initial seasoning is crucial for a well-rounded flavor profile.
In a small bowl, whisk together the balsamic vinegar, honey, minced garlic, and red pepper flakes if you enjoy a little heat. Set this mixture aside so it is ready to go as soon as the chicken is seared.
Heat the olive oil in a large skillet over medium-high heat. Place the chicken thighs in the pan, skin-side down. Cook for 5–7 minutes until the skin is crispy and golden brown. Flip the chicken and cook for another 4–5 minutes.
Pour the balsamic mixture into the skillet with the chicken. Bring the liquid to a simmer. Reduce the heat to medium-low and let the sauce bubble away for about 8–10 minutes. Occasionally spoon the sauce over the chicken as it thickens into a glaze.
Once the chicken reaches an internal temperature of 165°F and the sauce has thickened to your liking, remove the skillet from the heat. Let the chicken rest for 5 minutes before serving to allow the juices to redistribute.