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Preheat the oven to 350°F. Line a 9x13 inch baking pan with foil and coat with nonstick spray.
Beat the softened butter and both sugars together until light and fluffy, about 2 minutes. Add in the eggs and vanilla and mix until combined.
In a medium bowl, stir together the flour, salt, and baking soda. Gradually add the dry ingredients to the mixer on low speed until the dough comes together. Stir in the chocolate chips.
Press half of the cookie dough into the bottom of the prepared baking dish.
To make the caramel filling, melt the unwrapped caramels and sweetened condensed milk together over medium-low heat, stirring continuously until creamy and smooth.
Pour the caramel over the cookie dough in the pan and sprinkle with flaky sea salt.
Drop the rest of the cookie dough in small clumps over the top of the caramel.
Bake at 350°F for 25-30 minutes until golden and set in the center. Sprinkle with flaky sea salt after baking.
Cool completely before slicing into bars.