Keep TripIt when the bookings already exist and the job is one timeline. On October 27 the free column still organizes plans from your inbox, syncs a calendar, shares the trip, and allows 3 documents per trip. Pro at $49 a year is the alert layer: real-time flight alerts, fare-refund monitoring, a better-seat note, alternate flights, check-in and gate reminders, and 25 documents per trip. The page says the app is on iOS, including Apple Watch, and Android, including Android Wear, and that the itinerary opens offline. The Pro page says a 30-day trial, then $49 for a year. TripIt will not invent a city you have not booked.
Open Wanderlog when you are still deciding the days and you also want the bookings on the map. The October 30 homepage is still a map, a route, and a shared itinerary. It now says you can forward reservation emails to Wanderlog, or connect Gmail so hotel, flight, and other bookings are imported. Automatic Gmail scanning is listed under the Pro heading, and the page still prints no Pro price. TripIt's $49 alerts are not on that page.
Open Stardrift when you want a free planner that also talks about email. The October 20 homepage says the iOS app is free, that planning works on the web, and that it can organize bookings forwarded from email or connected from Gmail. The trip-planner page says planning is free and that booking connects you to the airline, hotel, or booking site. It does not mention Android. A generated day can still be wrong. That page was not reread on October 27.
Open Flighty beside TripIt, not instead of it, when the question is whether the inbound plane is late. On October 27 the homepage says the prediction uses the inbound aircraft and machine learning, up to 6 hours before the airline, on iPhone, iPad, Mac, and Apple Watch. Pro is $4.99 a month or $59.99 billed annually. The help page says the free first flight does not include TripIt import. Flighty does not hold the hotel, the car, or the dinner.
If you have not booked anything, you do not have a TripIt problem yet. Use a planner first, then forward the confirmations.