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Combine Italian seasoning and black pepper in a small bowl; rub all over the chicken.
In a 3-1/2- or 4-quart slow cooker, combine chicken, onion, mushrooms and garlic. Pour undrained tomatoes and vinegar over mixture.
Cover; cook on Low for 4 to 5 hours or on High for 2 to 2 1/2 hours.
If using Low, turn to High. Add squash (or zucchini) and bell pepper. Cover; cook for 30 minutes more.
Meanwhile, combine mayonnaise (or dressing) and pesto in a small bowl. Spread evenly over cut sides of flatbread. Transfer chicken to a cutting board. Thinly slice chicken. Arrange chicken slices on bottom half of bread. Using a slotted spoon, spoon vegetable mixture over chicken. Sprinkle with cheese. Add top half of bread. Cut into wedges.