#!/usr/local/bin/perl

use strict;
use warnings;

use Time::Local;
use POSIX qw(strftime);

my %flights;

while ( my $line = <DATA> ) {
    chomp $line;
    my ( $date, $num, $to, $from, $char, @times ) = split / /, $line;
    my $text = "$num $to $from $char";
    my ( $mday, $mon, $year ) = split /\./, $date;
    for my $time (@times) {
        my ( $hour, $min ) = split /:/, $time;
        my $epoch = timelocal( 0, $min, $hour, $mday, $mon, $year );
        push @{ $flights{$epoch} }, $text;
    }
}

for my $key ( sort keys %flights ) {
    my $time = strftime "%a %b %e %H:%M %Y", localtime($key);
    for my $flight ( @{$flights{$key}} ) {
        print "$time - $flight\n";
    }
}

_ _DATA_ _
30.07.2004 123456 Malaga Bielefeld C 12:15 11:31
23.07.2004 654321 Berlin Bielefeld D 13:00 12:58
04.07.2004 587931 Barcelona Bielefeld E 14:00 12:00
30.07.2004 356987 Muenchen Bielefeld A 12:50 12:00
30.07.2004 879652 Koeln Bielefeld B 12:55 12:15
30.07.2004 456987 Bonn Bielfeld H 14:00 11:55
05.08.2004 456789 Freiburg Bielfeld C 15:00 13:00
01.09.2004 336632 Berlin Bielefeld B 22:00 19:00