In a large bowl, use a hand mixer to combine the cream cheese and powdered sugar until well-combined. Beat in the vanilla extract.
In a small microwave-safe bowl, heat the chocolate chips in 30-second intervals, stirring after each interval, until melted. Let cool slightly. Add the melted chocolate to the cream cheese mixture and beat on low speed until just combined, then on high speed until smooth. Cover and refrigerate for at least 30 minutes.
Meanwhile, wash and dry the strawberries. Slice each strawberry in half lengthwise through the stem, leaving the stem intact. Using a small spoon or strawberry huller, hollow out the middle of each strawberry half, being careful not to go too deep.
Place the chilled cheesecake mixture in a piping bag with a decorating tip or a resealable plastic bag with a corner snipped off, then pipe into each strawberry half. Garnish with the mini chocolate chips.
Store in the refrigerator until ready to serve. These are best served within 2 hours of filling the strawberries, but I recommend waiting to fill the strawberries until right before serving.