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Season chicken with salt and pepper on both sides. Place flour in a shallow dish. Add chicken and turn to coat. Measure out 4 teaspoons of the flour to a small bowl and whisk in 1/4 cup port (or cranberry juice cocktail) until smooth (discard the remaining flour).
Heat 1 tablespoon oil in a large nonstick skillet over medium heat. Add the chicken and cook until browned on the outside and no longer pink in the middle, about 4 minutes per side. Transfer to a plate.
Add the remaining 1 teaspoon oil and garlic to the pan; cook, stirring, until fragrant, about 30 seconds. Add the flour-port mixture, the remaining 1/2 cup port (or juice), broth, dried cherries (or dried cranberries), olives, vinegar, brown sugar and oregano. Bring to a boil, stirring. Reduce heat to a simmer and cook, stirring occasionally, until the sauce has thickened, 4 to 6 minutes.
Return the chicken to the pan along with any accumulated juices. Turn to coat with sauce and cook until heated through, about 2 minutes. Serve the chicken with the sauce.