Preheat the oven to 425°F (220°C). Toss the butternut squash cubes with the olive oil, salt, and pepper on a large baking sheet.
Roast the squash 20 to 25 minutes, stirring once, until tender and lightly caramelized.
Whisk together the maple syrup, Dijon mustard, olive oil, apple cider vinegar, and salt until smooth.
Shred the rotisserie chicken meat, discarding skin and bones.
Toss the shredded chicken with about half the maple-mustard sauce.
Warm the tortillas in a dry skillet or over a low flame until pliable.
Layer each tortilla with kale, roasted squash, the sauced chicken, cranberries, and crumbled cheese, keeping the portion moderate.
Drizzle the remaining sauce over the filling, fold in the sides, and roll tightly. Slice in half and serve.