In a large bowl or a stand mixer, whisk whipping cream with powdered sugar and vanilla until stiff peaks form. Reduce speed to low and mix in mascarpone just until blended. Take care not to over beat since this will cause the cream to start to separate.

In a small bowl, combine espresso and amaretto. Dip ladyfingers one at a time in espresso mixture for 1 second, then allow to drain for 2 seconds and place in a single layer in the bottom of a loaf pan. With a rubber spatula, spread 1/3 of the cream mixture evenly over ladyfingers. Sprinkle with 1/2 cup chocolate chips. Repeat layers 2 more times until all cream and chocolate chips are used (there may be a few ladyfingers left over). Sprinkle with cinnamon and refrigerate for 30 minutes before slicing and plating. Leftovers may be refrigerated for up to three days.