$re = '/\bto\b(?:(?!\bto\b).)*?CITY\d+/s';
$str = 'John from beautiful CITY1 in sdfsf to dsfs in sf to abc CITY2 to CITY3 for 3 days';
$subst = "";
$result = preg_replace($re, $subst, $str);
echo "The result of the substitution is ".$result;
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for PHP, please visit: http://php.net/manual/en/ref.pcre.php