TripIt is worth installing free and worth paying for only if you fly often. Its free tier turns every forwarded booking email into one trip timeline, with airport maps and calendar sync. TripIt Pro, $49 a year after a 30-day trial, adds alerts that mostly watch a flight, so it pays off with flight count, not trip count.
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Plan a trip →Disclosure: MonkeyEatingMango, the product behind this blog, appears below as the planning half TripIt does not do. TripIt's features were read off tripit.com/web/free and tripit.com/web/pro on October 21 and 22, 2026; Inbox Sync details come from TripIt's help center.
- What it is: a booking organizer from Concur Technologies (SAP Concur), launched in 2006.
- Free: forward confirmations to plans@tripit.com, or connect an inbox, and get one timeline per trip.
- Pro: $49 a year as of October 2026: flight status alerts, seat and fare trackers, risk alerts, alternate flights.
- The catch: it plans nothing. No activities, no days, no routes.
- Safe? Inbox Sync uses OAuth, never your password, and can be revoked at any time.
Is TripIt free?
TripIt is free for organizing trips, and the free tier is the core product rather than a demo. Forward a flight, hotel, car or restaurant confirmation to plans@tripit.com and it lands in a chronological trip, or turn on Inbox Sync to have TripIt add plans from your inbox. The free tier also includes documents (photos, QR codes, PDFs; 3 per trip, 25 on Pro, per TripIt's help center), airport maps, a navigator between places, neighborhood safety scores, calendar sync and sharing by text or email, per tripit.com on October 22, 2026.
How much does TripIt Pro cost, and what does it add?
TripIt Pro costs $49 a year after a free 30-day trial, as of October 2026. Most of what it adds watches a flight, per tripit.com/web/pro on October 21, 2026:
| Stage | What TripIt Pro adds |
|---|---|
| After booking | Seat Tracker, Fare Tracker (a price drop after you book), Point Tracker, passport renewal reminder |
| Before leaving | Check-in reminder 24 hours ahead, Go Now (when to leave for the airport), risk alerts |
| On the move | Real-time flight status, alternate flights, terminal and gate updates, connecting-gate help, baggage claim info |
| Anytime | Inner Circle: shares your plans automatically with chosen family or colleagues |
Is TripIt Pro worth it?
TripIt Pro is worth it when flights are frequent, because most of its features do nothing on a trip without one. A traveler on two flights a month gets gate changes, seat openings and fare drops working all year, and one fare refund can cover the fee. A traveler on two vacations a year gets a handful of alerts.
| You | TripIt tier |
|---|---|
| Fly every few weeks, often with connections | Pro: the trackers and gate updates earn the fee |
| Take one to three leisure trips a year | Free: the timeline is the whole job |
| Share plans with a partner or assistant | Free sharing first; Pro's Inner Circle automates it |
| Need a day-by-day plan | Neither: TripIt plans nothing |
The 30-day trial settles it. Start it on a real trip with flights, count the alerts that changed a decision, and cancel before renewal if the answer is zero.
Is TripIt safe?
TripIt is safe to connect to an inbox by its stated design. Inbox Sync works with Gmail, Microsoft 365, Outlook and Yahoo Mail through OAuth, so TripIt never asks for or stores the email password, and access can be revoked from TripIt or the email provider at any time (TripIt help). It scans the headers of the main inbox for travel plans and parses only the emails that contain one. For Google accounts, TripIt says its use of the data follows Google's API Services User Data Policy, including the Limited Use requirements.
Inbox Sync is optional. Forwarding confirmations by hand to plans@tripit.com gives TripIt only the emails you choose.
What TripIt does not do
TripIt has no opinion about what to do on Tuesday. It suggests no activities and builds no days, routes or budgets at any tier, so it was left out of the 7-day Tokyo test behind the Oh-No Travel Index, which scores plans. Wanderlog Pro lists live flight updates too, as of October 2026, so for basic flight alerts the two overlap; TripIt Pro's edge is the seat, fare and risk trackers and the airport help. The Wanderlog vs TripIt comparison covers that pairing, and TripIt alternatives the wider field.
Disclosure: this is the product behind this blog, described the same way as TripIt, including its limits.
MonkeyEatingMango covers the half TripIt leaves out: answer 8 questions and it returns a dated plan with a time and a cost on every stop, free to read; downloads cost $0.99 per trip. It does not read booking emails or send flight alerts, so the bookings that come out of the plan still need an organizer like TripIt.
Last updated October 2026.
Written by Shobhit Shrivastava · Founder
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