Heat oven to 450°F and adjust oven rack to lowest position.
Line a large, rimmed baking sheet with aluminum foil and spray the foil with nonstick spray.
Add potatoes, onions, bacon to the baking sheet and drizzle with oil. Toss ingredients to coat with thoroughly with oil, and season with salt and pepper.
Set the vegetables in the oven (lowest rack) and cook 10 minutes.
While the vegetables roast, heat 2 tablespoons oil in a large cast iron (if available) skillet set over medium-high heat.
Pat the chicken dry with paper towels and sprinkle with salt and pepper. When the oil is hot, press the chicken (skin-side down) in the skillet. Cook until the skin is a dark golden brown, about 10 minutes. Transfer chicken, skin-side up, to a paper towel-lined plate. When all chicken has partially cooked, transfer the chicken (skin-side up) to the sheet pan with the vegetables.
Roast an additional 15-30 minutes or until the internal temperature of the chicken registers 175°F-180°F on an instant-read meat thermometer.
While the chicken/vegetables finish cooking, drain all except 2 tablespoons fat from the skillet. Turn heat to medium and add minced shallot, rosemary, ¼ teaspoon kosher salt and ¼ teaspoon ground black pepper. Cook until shallot tender, 1-2 minutes. Add figs, Madeira and wine and cook until slightly reduced, about 3 minutes. Serve fig sauce over the roasted chicken and vegetables.
Garnish with chopped fresh parsley or thyme, if desired.
Serve with pieces of crusty French baguette.