In a mixing bowl, combine the cream cheese, powdered sugar, and vanilla extract. Use a fork or whisk to blend until smooth and creamy.
Gently fold in the diced strawberries until evenly distributed throughout the cream cheese mixture.
Lay a flour tortilla flat on a clean surface. Place about 3 tablespoons of the strawberry cheesecake filling in the center of the tortilla.
Fold the sides of the tortilla over the filling and then roll it up tightly from the bottom to the top. Secure with a toothpick if necessary. Repeat for remaining tortillas.
In a frying pan or deep fryer, heat the vegetable oil over medium heat until it reaches 350°F (175°C).
While the oil heats, combine the granulated sugar and ground cinnamon in a small bowl.
Carefully place 2-3 chimichangas in the hot oil, being cautious not to overcrowd the pan. Fry for 2-3 minutes per side, or until golden brown.
Using a slotted spoon, remove the chimichangas from the oil and let them drain on paper towels.
While still warm, roll each chimichanga in the cinnamon sugar mixture until well-coated.
Allow to cool slightly before serving. Enjoy with additional strawberries or whipped cream if desired!