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Season chicken all over with ½ teaspoon salt and ½ teaspoon pepper. Wrap 2 slices prosciutto around each piece of chicken, gently pressing prosciutto against chicken to adhere. Pour flour on a shallow plate. Dredge chicken in flour, shaking off any excess.
In a 12" skillet over medium-high heat, heat oil. Cook chicken, turning halfway through, until chicken and prosciutto are golden and prosciutto is crisp, 2 to 3 minutes per side. Transfer chicken to a plate.
Pour vinegar into skillet and cook, scraping up browned bits, until almost completely reduced, about 30 seconds. Add stock and cook, stirring occasionally, until reduced by half, about 2 minutes. Return chicken to skillet and cook, turning a few times, until sauce thickens, about 2 minutes more. Remove from heat.
Transfer chicken to a platter. Scatter tomatoes, mozzarella, and basil over top; season with ¼ teaspoon salt. Drizzle sauce remaining in skillet over and serve.