Preheat and Prepare Pans:

Preheat your oven to 350°F (175°C). Grease and flour two 9-inch round cake pans.

Make the Chocolate Cake:

In a large bowl, mix flour, cocoa powder, sugar, baking powder, baking soda, and salt. Add eggs, milk, oil, and vanilla to the flour mixture. Mix on medium speed for 2 minutes. Stir in boiling water until the batter is thin and smooth. Divide the batter evenly between the prepared pans.

Bake the Cake:

Bake for 30-35 minutes or until a toothpick inserted in the center comes out clean. Let the cakes cool in the pans for 10 minutes, then turn them out onto wire racks to cool completely.

Prepare the Whipped Cream:

In a chilled bowl, whip the heavy cream with powdered sugar and vanilla until stiff peaks form.

Assemble the Cake:

Place one layer of cake on a serving plate. Spread half of the cherry pie filling over the layer. Add a layer of whipped cream on top of the cherry filling. Place the second layer of cake on top, spread the remaining cherry pie filling, and top with more whipped cream. Garnish with fresh cherries and chocolate chips.

Chill:

Refrigerate the cake for at least 1 hour before serving to let the layers set.