In a medium bowl, beat cream cheese, sugar, vanilla, and 1/4 cup caramel sauce until smooth and creamy.
Spoon about 2–3 tablespoons of the cheesecake mixture onto the lower third of each tortilla.
Fold the sides in and roll up tightly like a burrito. Brush the edge with beaten egg to seal.
In a shallow bowl, mix sugar and cinnamon for coating.
Heat 2 inches of vegetable oil in a deep skillet or pot to 350°F (175°C).
Fry chimichangas in batches for 2–3 minutes, turning until golden brown and crispy.
Remove with a slotted spoon and drain briefly on paper towels.
While still warm, roll chimichangas in the cinnamon sugar mixture to coat.
Drizzle with extra caramel sauce and serve with whipped cream if desired.