Microsoft will soon roll out a new preview feature called Travel savings for Outlook.com premium users. This new feature will monitor your upcoming hotel reservations and past and upcoming flight reservations via email confirmations you received. For hotel reservations, Outlook will look for the lowest rate possible, based on price changes to your room between when you book and when your stay begins. For flight reservations, Outlook will automatically file compensation claims with the airline if flight is delayed or cancelled.
When generally available, this feature will be available only for Office 365 Home or Personal subscribers. For now, this feature will be enabled only for users in the United States, Canada, and European Union who got an invitation offer via email or in-product message in Outlook.com.
This feature is powered by Service Technologies, you can read about the supported airlines and other details here.