In a large bowl, use an electric mixer to whip the heavy cream until stiff peaks form. In a separate bowl, beat together the softened cream cheese, powdered sugar, and vanilla extract until smooth and creamy.
Gently fold the whipped cream into the cream cheese mixture until fully combined, creating a light and fluffy filling. Stir in the mini chocolate chips.
In a 9x13 inch dish, start with a layer of chocolate sandwich cookies at the bottom. You can either leave them whole or break them in half to fit better.
Spread half of the cream mixture over the layer of cookies, smoothing it out with a spatula.
Add another layer of cookies on top of the cream mixture. Follow with the remaining half of the cream mixture. Top with one final layer of cookies.
Cover the dish with plastic wrap and refrigerate for at least 4 hours or overnight for best results, allowing the cookies to soften and flavors to meld.
Before serving, sprinkle the top with crushed chocolate sandwich cookies and drizzle chocolate syrup over the lasagna.