Gather all the ingredients listed above. Make sure your vanilla ice cream is slightly softened for easier blending.
In your blender, combine the 4 cups of vanilla ice cream and 1/2 cup of whole milk. Blend on medium speed until the mixture is smooth and creamy. You want it to be thick but pourable.
Add the lightly crushed Oreo cookies to the blender. Pulse a few times to mix them into the milkshake but be careful not to over-blend. You want to maintain some cookie chunks for texture.
Pour the milkshake into your favorite glasses. Top each glass with a generous dollop of whipped topping and finish with a maraschino cherry on top.
Grab a straw, dig in, and enjoy your homemade Chick-fil-A Cookies and Cream Milkshake!