Prepare the strawberry filling by combining strawberries, cream cheese, powdered sugar, and vanilla extract in a mixing bowl.
Arrange the tortillas on a clean surface and spoon an equal amount of the strawberry mixture onto the center of each tortilla.
Fold the sides over the filling, then roll the tortilla tightly from the bottom to create a sealed chimichanga.
Heat vegetable oil in a large skillet over medium heat until shimmering.
Once the oil is hot, carefully add the chimichangas, seam side down, and fry until golden brown on all sides.
Using a slotted spoon, remove the chimichangas from the oil and place them on paper towels to drain excess oil.
Drizzle with chocolate sauce and serve immediately, optionally topped with whipped cream.