Love TripIt Pro! In fact, as I travel 50% of the time for work, I live by TripIt Pro! Pros of the Pro version that I use almost every day: - Others in your "inner circle" (e.g. my wife) are notified of new travel plans, and can see your travel plans, even if they are using the free version. - All my airplane trips are monitored, with me notified of delays, often faster than the notifications from the airline apps or texts! - Im given alternate flights, so when things go wrong I know exactly what my options are, before I talk with the airline rep. - Your inner circle can see your flight statuses (even if they are using the free version). - The seat tracker integration is great. If Im stuck in a middle seat on a cross-country or trans-continental flight, seat tracker tells me the instant a window or aisle seat opens up. Things in the free version I use all the time: - TripIt has all my travel plans in one place, no need to bounce from app to app looking for hotel addresses, etc. - In Outlook 2016, i subscribe to the TripIt iCal, so all my plans are in my calendar. What makes this better than the Microsoft or Google inbox monitoring, is that each reservation (flight, train, hotel, etc) is listed on its own: not the whole time in between! Cons of the Pro version: - Yes, it is relatively expensive. All the Pro features (except monitored trip sharing) are available in other free apps. The difference is that TripIT puts them in one place, monitors your flights, and shares all that with your loved ones. - TripIt should monitor train trips too (for how much it costs) with statuses (on schedule, delayed, etc). Amtrak has this feature in their app, so the data is available! - The same goes for other train travel, both commuter and regional (including other countries). The data is available for a bunch of local, country-wide and regional train systems, like French SCNF, Swiss SBB, England, NJ Transit, New York MTA MetroNorth, New York LIRR, Boston MBTA, Chicago MTA, in their apps. No reason train travel shouldnt be monitored in TripIt.