its a problem that is easily over come but is related to nesting and visual tree of wpf/Silverlight. To solve the problem you have to use abit of CM wizardry to overcome the problem:
Bold part is the key to your nest issues...
<telp:RadContextMenu.ContextMenu>
<telp:RadContextMenu x:Name="ScheduledFlightMenu" cm:Action.TargetWithoutContext="{Binding DataContext, ElementName=ScheduledFlights}">
<telp:RadContextMenuItem Content="edit" cm:Message.Attach="EditFlight($dataContext)" />
<telp:RadContextMenuItem Content="delete" cm:Message.Attach="DeleteFlight($dataContext)" />
</telp:RadContextMenu>
</telp:RadContextMenu.ContextMenu>
cm:Action.TargetWithoutContext="{Binding DataContext, ElementName=ScheduledFlights}"Bold part is the key to your nest issues...