Combine raisins and whiskey in a small bowl. Let sit until raisins are plump, about 30 minutes and up to overnight.
Preheat oven to 350°F. Grease 10-inch cast iron skillet with nonstick cooking spray.
Combine milk, 1 cup granulated sugar, vanilla extract, evaporated milk, eggs, and salt in a large bowl. Whisk to combine. Add raisin-whiskey mixture and stir.
Add bread cubes, pressing down gently to moisten; let stand about 30 minutes, stirring occasionally.
Divide mixture among prepared cast iron skillet. Combine remaining 2 tablespoons granulated sugar and cinnamon; sprinkle over pudding. Transfer to oven and bake until custard is set and pudding is golden brown, about 35 minutes.
Meanwhile, make caramel sauce: Combine granulated sugar and ⅔ cup water in a small saucepan over medium-high heat.
Stir continuously until sugar dissolves.
Simmer, not stirring, until sugar mixture is golden, about 18 minutes.
Remove from heat and carefully add butter and cream cheese, stirring constantly with a whisk until all clumps are dissolved. Mixture will bubble vigorously. Stir in whiskey, milk, and salt to taste.
Serve bread pudding warm with caramel-whiskey sauce.