Preheat waffle iron according to manufacturer instructions.

In a large bowl, whisk together flour, sugar, baking powder, and salt.

In another bowl, beat eggs and combine with milk, melted butter, and vanilla extract.

Gradually pour wet ingredients into dry ingredients, mixing until just combined. Fold in chocolate chips.

Pour batter into preheated waffle iron and cook according to manufacturer instructions until waffles are golden brown and crisp. Repeat with remaining batter.

To make caramel drizzle, heat sugar in a small saucepan over medium heat, stirring until melted and amber in color. Add butter and stir until combined. Slowly whisk in heavy cream and a pinch of salt. Cook for 1–2 minutes until smooth.

Drizzle warm caramel over waffles and serve immediately with optional toppings.