Cook the bacon in a large wide pot or Dutch oven over high heat, stirring, until crisp, about 4 minutes. Remove with a slotted spoon to paper towels to drain; leave the drippings in the pot.
Season the chicken generously with salt and pepper and dust with the flour. Add skin-side down to the pot with the bacon drippings; cook until golden brown, 5 to 8 minutes.
Meanwhile, trim the okra and thinly slice the onion. Remove the chicken to a plate; add the okra, onion, garlic, oregano and red pepper flakes to the pot. Cook over medium-high heat, stirring occasionally and scraping up any browned bits, until the onion starts softening, about 4 minutes. Crush the tomatoes into the pot with your hands and stir well; bring to a boil. Nestle the chicken skin-side up in the sauce. Cover, reduce the heat to medium low and simmer until the chicken is cooked through and the okra is tender, 15 to 20 minutes.
Stir the reserved bacon into the okra mixture and season with salt and pepper. Serve the chicken and okra mixture with cornbread.