Line the bottom of a 9-inch springform pan with CHIPS AHOY! Cookies, breaking apart to fill in the small spaces.
In the bowl of a stand mixer, mix cream cheese, sugar, vanilla and peppermint extract together until smooth, using the paddle attachment. Scrape the sides and mix again briefly. With the mixer on low, slowly stream in heavy cream to mix evenly and ensure no lumps form. One all the cream has been added in, scrape the sides and bottom. Increase speed to high and whip until stiff peaks form, 3-4 minutes.
Spread 1/4 of this cream mixture over the cookies.
Continue layering cookies and cream until you have 4 layers of each. Cover with plastic wrap and refrigerate 8 hours to overnight. Run a sharp knife along the edge of the cake before unlatching the springform to remove the sides.
Garnish with peppermint whipped cream, crushed candy canes and chocolate syrup. Serve.
To make the peppermint whipped cream: whip 1 cup of heavy cream with 1 teaspoon peppermint extract, 1/2 teaspoon vanilla and 1/4 cup powdered sugar until stiff. Use as desired.