Open TripIt when the bookings already exist and they are not all flights. On October 27, 2026 the pricing page still lists the organizer as free. You forward confirmations to plans@tripit.com. The free column includes the itinerary, inbox import, calendar sync, sharing, and 3 documents per trip. Pro is $49 a year for real-time flight alerts, fare-refund monitoring, a better seat, alternate flights, check-in and gate reminders, airport navigation, and 25 documents. The page says iOS, including Apple Watch, and Android, including Android Wear, plus offline access. The Pro marketing page says a 30-day trial, then $49 for a year. The pricing page does not spell out that trial. TripIt does not tell you the inbound aircraft is late before the airline does.
Open Flighty when the question is the airplane and the phone is an Apple device. The homepage says iPhone, iPad, Mac, and Apple Watch, and that the download is free. It tracks the inbound aircraft 25 hours out and uses machine learning to predict a late-aircraft delay up to 6 hours before the airline posts it. Pro is $4.99 a month or $59.99 billed annually. The pricing FAQ says free tracking stays after the trial flight, and that alerts before the airlines, gate predictions, and imports from email, calendar, and TripIt are Pro. A help page says the complimentary first flight unlocks Pro tracking and excludes those three imports. The homepage does not name Android. Flighty does not hold the hotel, the car, or the dinner.
Use both when you fly often and the rest of the trip has confirmations. TripIt is the timeline. Flighty is the aircraft. Connecting them costs Flighty Pro, not the free first flight. A company booking tool such as Navan, Perk, or Concur is a third job: it is how the company buys the ticket, not how you watch it.
If nothing is booked yet, neither page is the planner. Book first, then forward the mail to TripIt, and add Flighty if the delay warning is worth the Pro price.