Whip the whipping cream with an electric mixer until stiff peaks form. Set aside.
In a large bowl, combine the condensed milk, vanilla extract, gingerbread spice and chocolate chips. Add a large dollop of whipped cream and mix until well combined. Add the remaining whipped cream and gently fold to combine. Add the crushed gingerbread men and fold to combine.
Pour the ice cream into a plastic container, seal with a lid and freeze for 6 hours until firm.