Preheat 2-sided tabletop grill. Combine, in zip-top bag, chicken, 1/4 cup dressing and garlic. Wash hands. Seal bag and knead to coat chicken. Let sit 10 minutes to marinate.
Season with salt and pepper the breast halves. Coat both sides of grill with cooking spray; use tongs to add chicken. Close lid and grill 3-4 minutes. (Or 6-8 minutes, turning once, on regular grill.)
Place bacon on top of cutlets; grill 1-2 more minutes to heat.
Set bacon aside. Cut chicken into strips. Fill center of each tortilla with cheese, lettuce, tomatoes, chicken and bacon. Top with remaining dressing. Fold bottom of tortillas up about 1 inch and then roll up.