In a mixing bowl, beat the softened cream cheese with an electric mixer until it becomes smooth and creamy.
Gradually add the sweetened condensed milk to the cream cheese, mixing well until fully incorporated and smooth.
Add the creamy peanut butter and vanilla extract to the mixture. Continue to mix until everything is well combined and fluffy.
Carefully fold in the thawed whipped topping using a spatula.
Gently fold in half of the chopped peanut butter cups, saving the other half for topping.
Transfer the mixture to your serving dish, smoothing out the top. Drizzle the chocolate syrup over the dip and sprinkle the remaining peanut butter cups on top.
Refrigerate the dip for at least one hour to allow the flavors to meld together.