Make the cookie bowl: Preheat the oven to 350˚. Line a 3-quart metal bowl (with an 8-inch diameter at the top) with foil, leaving a 1-inch overhang. Coat the foil with cooking spray; set aside.
Whisk the flour, baking soda and salt in a medium bowl. Beat the butter and brown sugar in a large bowl with a mixer on high speed until light and fluffy, about 2 minutes. Beat in the egg and vanilla. Reduce the mixer speed to low and beat in the flour mixture until just combined. Stir in 3/4 cup mini chocolate chips. Working with a small handful at a time, press the dough into the bottom and up the sides of the foil-lined bowl to cover, stopping 1 inch from the rim of the bowl. Freeze until set, about 15 minutes.
Line the dough in the bowl with parchment paper and fill with enough dried beans to reach the top edge of the dough. Bake until the bottom and sides of the cookie bowl are set and the parchment can be removed without sticking, about 1 hour. Remove the parchment paper and beans. Reduce the oven temperature to 325˚ and continue baking until the bottom of the cookie is dry but still soft, 15 to 25 minutes. Transfer to a rack and let cool completely in the bowl, about 30 minutes. Lift the cookie out of the bowl using the foil overhang, then remove the foil.
Combine the remaining 1 cup mini chocolate chips and the coconut oil in a heatproof bowl set over a saucepan of simmering water; cook, stirring, until melted. Remove from the heat and whisk until smooth. Let cool 10 minutes. Brush the inside of the cookie bowl with some of the melted chocolate. Freeze until set, 10 to 20 minutes. Reserve the remaining melted chocolate for topping.
Make the milkshake: Blend the ice cream, liqueur and bourbon in a blender. Pour into the cookie bowl; top with whipped cream and the remaining melted chocolate.