Heat a heavy medium skillet over medium heat and melt butter. Add sugar and cinnamon and continue cooking until browned, about 4 to 5 minutes. Add apples and pears and cook until slightly softened, another 6 minutes. Add tequila and continue cooking until browned, another 5 to 7 minutes.
Place 1 tortilla on a plate, and spoon about 1/6th of the apple/pear mixture into the center. Roll them and tuck the ends, egg-roll style, and secure them with toothpicks.
In another skillet, heat vegetable oil over medium heat until a drop of water sizzles and pops in the oil, about 350 degrees F, and fry each chimichanga until browned and crispy, about 2 to 3 minutes per side. Transfer them to a plate lined with paper towels to drain. Remove the toothpicks and cut in half.
Serve hot, topping with a scoop of the vanilla ice cream.