In a bowl, beat the cream cheese, sour cream, sugar, and vanilla until smooth.
Spread 2 tablespoons of the cream cheese mixture down the center of each tortilla.
Top with 2 tablespoons of cherry pie filling.
Fold in sides and roll up each tortilla tightly like a burrito.
Heat oil in a deep skillet over medium-high heat.
Fry chimichangas until golden brown and crispy, about 2–3 minutes per side.
Remove and drain on paper towels.
Mix cinnamon and sugar together and roll each warm chimichanga in the mixture.
Serve warm or chilled.