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Place the peanut butter cups in the freezer to harden before making the cookies.
Preheat oven to 350°F and line 2 baking sheets with parchment paper.
In a medium bowl, combine flour, baking soda, and salt. Set aside.
In the bowl of a standing mixer with the paddle attachment or a handheld mixer, combine butter and sugars, mixing until light and fluffy (1-2 minutes).
Add in the egg and vanilla extract, and beat until just combined (do not over-mix!).
Mix in the dry ingredients until a dough forms. Stir in the chocolate chips and mix until just combined.
Use a medium cookie scoop or spoon to make 1.5 tablespoon sized balls and place them on the baking sheet around 3-4 inches apart.
Remove the peanut butter cups from the freezer. Gently press a peanut butter cup into each ball of dough, then cover with another 1-1.5 Tablespoons of dough to seal the edges. Add a few more chocolate chips on top of the dough if desired.
Bake the cookies (one sheet at a time for even baking) for 8-11 minutes. Remove them from the oven when the edges look set. They should look a little under-baked in the middle! Remove from the oven and leave them on the baking sheet for 5 minutes, then transfer to a cooling rack to cool completely. Enjoy!