Heat the olive oil in a large, nonstick or cast iron skillet over medium high.
Season the chicken with salt and pepper. Add to skillet and cook until lightly browned and cooked through, about 5 minutes. Transfer to plate.
Reduce skillet heat to medium low. Add the chopped bacon and cook until crisp and brown, about 8 minutes. With a slotted spoon, transfer the bacon to a paper towel-lined plate
Discard all but 1 1/2 tablespoons bacon fat from the pan and increase heat back to medium high.
Add Brussels sprouts, sweet potato, and onion to skillet. Cook, stirring occasionally, until crisp-tender and the onions are beginning to look translucent, about 10 minutes.
Stir in the apples, garlic, thyme, and cinnamon. Cook 30 seconds, then pour in 1/2 cup of the broth. Bring to a boil and cook until evaporated, about 2 minutes.
Return chicken to the skillet with remaining chicken broth. Cook until heated through, about 2 minutes.
Transfer to serving dish. Sprinkle bacon on top of chicken and vegetables. Serve hot.