I'm a huge fan of TripIt. It scans my gmail account for confirmation emails, and I just forward flight, hotel, care rental, etc. confirmation emails sent to other accounts (eg work email) and voila! Integrates with Outlook calendar (but in its own calendar rather than my default). Still using the free version but considering the upgrade to Pro. The version I have installed still looks up flight status, a feature that was apparently disabled in a recent software update. (Good lesson about reading the reviews before updating apps.)