I've been using the free TripIt service for many years. I reviewed TripIt back in 2013, and while the service and the app have improved since then, the basic idea is the same. When you make a travel reservation and receive the email from the airline, hotel, rental car agency, train, etc., you simply forward that email to TripIt. The service recognizes you from your email address, reads and understands the content of those emails, and prepares an online itinerary for your trip. With the free TripIt app on your iPhone (or iPad), all of your travel info is in one place. Thus, if you are in the middle of your trip and need to find the name or address of your hotel, or a reservation number, everything is in one place in the TripIt iPhone app. It is a like a virtual travel agent which provides all of the core basic features. I love the service and recommend it to everyone.
TripIt Pro costs $49 a year, and it adds premium services to look out for you before and during your travel, much like a more sophisticated travel agent might do. The company gave me a free demonstration account earlier this year so that I could try it out, and I've used the service in connection with several trips over the Summer, Fall and Winter of 2016. I enjoyed the service, and I think that it is worth it for any frequent traveler. Here are the key features of the service.
TripIt Pro constantly monitors your travel reservations, and if anything changes, you are notified immediately. The value of this service to you will of course depend upon whether anything goes wrong during your travel. If something does go wrong, TripIt Pro is incredibly valuable and the service can pay for itself with just one alert.
In June of 2016, this feature was incredibly valuable for me. I was traveling to Miami along with many other attorneys at my law firm, and I was on an early morning flight. When I woke up, I saw an email from TripIt Pro alerting me that my direct flight had been cancelled.
The email gave me a link to get a list of alternative flights, and included phone numbers for the airline to make changes. Even though the airline itself never sent me a notification of the cancellation, TripIt Pro gave me the information that I needed to call and book an alternative flight. The alternative flight was inconvenient — to go from New Orleans to Miami, I had to first fly to Dallas — but at least I was able to (barely) make my meeting in South Florida later on that day. Many of my partners didn't find out about the cancellation until they got to the airport, at which time many of the alternative flights were already taken, and some of them missed the meeting entirely.
TripIt Pro gives you other flight alerts as well. It tells you when it is time to check in — something that most airlines tell you too, but the TripIt Pro email usually arrived before the airline one did, if that makes a difference to you.
Flight delays and cancellations happen far more often than any of us would like. But with immediate notification of any problems, at least you can be one of the first in line to make alternative arrangements.
Because I don't live in a city with a major hub airport, a large number of my flights involve connections through cities like Atlanta. When I land, I want to know information such as the time of my next flight, the gate at which I will be landing, and the gate out of which my next flight will leave. Of course virtually every airline has its own app or website that you can manually access to load all of this information, but sometimes those apps are slow to use. TripIt Pro sends you an email immediately upon landing on your first flight with all of the information that you need to make your connection, including gate information and whether the next flight is on time.
I found it very convenient to have this connection information pushed directly to me so that I didn't't have to do any extra work to find the key information that I needed.
I've been lucky enough for the past few months to get a good seat at the time that I booked my flight. If you are not as lucky, TripIt Pro includes a Seat Tracker service. Tell the service what kind of seat you are looking for (exit row, aisle, window, specific cabin, front of the plane, etc.) and TripIt Pro will notify you when that seat becomes available. You'll have to contact your airline to make the change, but at least you will know when it is the right time to do so.
TripIt Pro offers other features that didn't appeal to me, but maybe they would appeal to you. A Point Tracker service lets you track your travel points in one spot. (I find it more useful to just manage this through each specific airline, hotel, train, etc. service.) A flight refund service alerts you if a cheaper flight becomes available and you are ever eligible for a refund. (Does this ever really happen for anyone?) A sharing feature let's you share travel information with others. (Even with the free TripIt service, I just use the TripIt website "print" my travel itinerary to a PDF file and then I share that PDF file with others, without using the Pro sharing features.) And there are some discounts for other travel services if you use TripIt Pro.
It is nice that TripIt Pro offers additional features, but I think for most people the question is whether it is worth $50 a year to you to get immediate notification of delays or cancellation in your travel plans. If you travel often, and mentally divide up that $50 price among each of your different flights, then I suspect many frequent fliers would consider this a bargain. Even just one cancellation can cause a lot of distress for you, and with an immediate alert at least you can start working on a solution to the problem ASAP. The other TripIt Pro features are not in themselves worth $50 to me, but they are nice bonuses that increase the overall value.
Everyone who travels should check out the free TripIt app. If you are a frequent traveler, I encourage you to consider adding the TripIt Pro service.