Combine the milk, amaretto and sugar in a medium saucepan and bring to a near simmer over medium heat, stirring until the sugar dissolves.
While the milk is heating, place the chopped chocolate in a metal bowl and set the bowl over the saucepan of milk, stirring until the chocolate is melted and smooth.
Check every now and then to make sure the milk is not simmering.
Whisk the melted chocolate into the hot milk mixture and keep warm.
Whisk the whipping cream in a large bowl until soft peaks form.
Place one scoop of ice cream in each of four bowls.
Pour the hot chocolate mixture over the ice cream and top with the whipped cream.
Serve immediately with spoons.