Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
In a large mixing bowl, beat softened butter with brown sugar and granulated sugar until creamy.
Add eggs and vanilla extract, mixing until smooth.
In a separate bowl, whisk together flour, baking soda, baking powder, and salt.
Gradually add dry ingredients to wet mixture, stirring until just combined.
Fold in chocolate chips.
Using about 2 tablespoons of cookie dough, flatten into a disc. Place one Halloween Oreo on top, then cover with another 2 tablespoons of cookie dough, sealing edges around the Oreo.
Place stuffed cookies on prepared baking sheets, spaced 2–3 inches apart.
Optional: add Halloween sprinkles on top of the cookie dough for festive flair.
Bake for 12–14 minutes, or until edges are golden brown but centers are still soft.
Cool on baking sheets for 5 minutes before transferring to a wire rack.
Serve warm for a gooey Oreo center or let cool completely for a chewy surprise inside.