Simpler way of showing, hiding & disabling elements
Edit: now that you have shared your html I could make a better response ...     http://jsfiddle.net/EjBW7/2/

There is a lot of repeated code, you could write some functions to avoid repeating the code, the branches in the second block seem redundant. You could use jquery's ability to target multiple elements in one selector.

setCheckboxValue = function (selector, enable)
{
    return $(selector).attr('checked', enable);
}

$("#chReportData").click(function(){

 if($("#chReportData").is(':checked') ){
      console.log('#chReportData show');
     $("#reportDataOptions").show();
 } else {
     console.log('#chReportData hide');

     $("#ReportDataStatusOptions, #reportDataOptions").hide();
     setCheckboxValue('#chkReportPermission, #chReportDataStatus, #chReportDataCummulative, .allowedUpload, .allowedDelete', false);
 }
});

$("#chReportDataStatus,#chReportDataCummulative").click(function() {
  if ($("#chReportDataStatus").is(':checked') ) {
       console.log('#ReportDataStatusOptions show');
    $("#ReportDataStatusOptions").show();
 } else { 
     console.log('#ReportDataStatusOptions hide');
    $("#ReportDataStatusOptions").hide();
    setCheckboxValue('.allowedUpload, .allowedDelete', false);
 }
});