In a large skillet, cook the bacon over medium heat until crisp; drain, reserving 3 tablespoons of the bacon fat in the skillet. Whisk in the vinegar, sugar and mustard; season with pepper. Transfer to a medium bowl. Finely chop the bacon.
Spread the mayonnaise evenly on the tortillas. Layer with the bacon, cantaloupe (placed horizontally), onion and 2 cups lettuce. Roll up the tortillas lengthwise; secure with toothpicks and cut in half. Add the remaining lettuce to the bowl of dressing and toss. Serve the wraps with the salad.