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Arrange a rack in the middle of the oven and heat the oven to 400°F. Pat 4 bone-in, skin-on chicken thighs dry with paper towels and season all over with ½ teaspoon of the kosher salt and ¼ teaspoon of the black pepper.
Drizzle 1 tablespoon olive oil into a 10-inch or larger oven-safe skillet. Add the chicken, skin-side down. Cook undisturbed over medium heat until the skin is well-browned and crisp, about 15 minutes. Meanwhile, trim 1 pound Brussels sprouts and cut in half lengthwise. Cut ½ medium red onion into 1-inch chunks. Mince 2 garlic cloves and mix it with 2 tablespoons of the hot honey in a small bowl.
Transfer the chicken to a plate, skin-side up. Increase the heat to medium-high. Add the Brussels sprouts and red onion to the skillet. Season with the remaining ½ teaspoon kosher salt and ¼ teaspoon black pepper. Cook, stirring occasionally, until charred in spots, 3 to 4 minutes. Remove from the heat.
Nestle the chicken on top of the vegetables. Spoon the garlic-honey mixture on top of the chicken and use the back of the spoon to spread it evenly. Roast until the chicken is cooked through, 8 to 10 minutes. Drizzle the remaining 1 tablespoon hot honey over the chicken and vegetables. Garnish with red pepper flakes, if desired.