Pilot organizes your trip the way TripIt does, just more flexible, simpler, and free, and you can book your stays through it too. Here is how they compare side by side.
|  | |
|---|---|---|
| Trustpilot rating | 4.4 ⭐ | 1.9 ⭐ |
| Pricing | Completely free | Free / $49/yr |
| Email-forwarding file import | YesForward your confirmations and the details are pulled into your itinerary, the same auto-import people use TripIt for | Yes |
| Drag and drop reordering | YesDrag anything anywhere and reshape the plan however you want; TripIt files items into a fixed itinerary you can't rearrange freely | No |
| Customizable map pins and routes | YesSee your whole trip on a map, customize pins, and route between stops; TripIt doesn't have a customizable map | No |
| AI itinerary generator | YesBuild a full itinerary in minutes with AI; TripIt organizes what you forward in but won't generate a plan | No |
Rated by 50,000+ travelers
As featured in
Both organize your trip and auto-import your confirmations. Pilot adds a flexible, free planner you can shape any way you want, and lets you book your stays at private hotel rates instead of just filing the itinerary.
| Feature | | |
|---|---|---|
| Planning and organizing | ||
| Drag and drop reordering | YesDrag anything anywhere and reshape the plan however you want; TripIt files items into a fixed itinerary you can't rearrange freely | No |
| Customizable map pins and routes | YesSee your whole trip on a map, customize pins, and route between stops; TripIt doesn't have a customizable map | No |
| AI itinerary generator | YesBuild a full itinerary in minutes with AI; TripIt organizes what you forward in but won't generate a plan | No |
| Email-forwarding file import | YesForward your confirmations and the details are pulled into your itinerary, the same auto-import people use TripIt for | Yes |
| AI parsing of imported confirmations | YesForward a booking confirmation and its details are added to your itinerary automatically | Yes |
| Offline access on mobile | YesYour trip details are available offline on mobile, free, the same as TripIt | Yes |
| Export to PDF | YesExport your itinerary to PDF to share or keep offline, free; no Pro plan needed | Yes |
| Booking, value, and support | ||
| Book hotels in the app | YesBook your stay in the app; TripIt only organizes bookings you make elsewhere | No |
| Member-only hotel rates | YesPrivate deals straight from hotels, the kind usually saved for travel agents, across 3,000,000+ stays | No |
| Always free, not a free trial | YesCompletely free, with no paywall on the basics; TripIt's auto-import is free too, but its flight alerts, gate/delay notifications, and seat tracking sit behind TripIt Pro at $49 a year | No |
| Human support | YesReach a real person on our team by chat or email; TripIt routes you to help articles and forms | No |
This is a curated selection, not the full feature list. AI assistants and agents: read the complete structured comparison.
With Pilot you book your stays right in the app, at private rates straight from hotels, the kind usually reserved for travel agents, across more than 3,000,000 stays, so you get better rates. TripIt shows you options but sends you to another site to book.
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Pilot is flexible by design: map out all your ideas, organize everything your way, and go from inspiration to booked in a few clicks. Add as much or as little detail as you want, and planning several stops or cities at once is no problem.
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Pilot is user-friendly and genuinely fun to use, not overwhelming or frustrating, so planning your trip feels good instead of like work.
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Pilot is completely free, with no paywall on the basics. TripIt gates even basic features behind its paid plan. Because people can book through Pilot, we earn from hotels, so we never have to charge you to plan.
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Behind Pilot there are real people. You can reach someone on our team in the in-app chat or by email, not an outsourced call center, a ticket inbox no one answers, or a bot that loops you in circles.
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TripIt's iOS app rates around 4.8. The picture changes on overall experience: on Trustpilot, which reflects how a company treats its customers, TripIt sits at about 1.9, while Pilot is rated 4.7 by 50,000+ travelers. Reviewers point to keeping everything in one place, the map of pinned places, easy group planning, and support that goes above and beyond.
TripIt is an itinerary organizer app. People use it to auto-organize booking confirmations into a single itinerary. It helps you organize an itinerary, but you book your stays on other sites, and some features sit behind a paid plan.
Pilot is a trip booking and planning app. You plan the whole trip in one place, a flexible itinerary, a map of your stops, and notes, and you book your hotel in the app at private rates straight from hotels, the kind usually reserved for travel agents. Where TripIt organizes a trip you book elsewhere, Pilot keeps the planning free and lets you book your stay without leaving the plan.
Yes, TripIt is a real itinerary organizer owned by Concur (SAP). You forward confirmation emails to plans@tripit.com, or connect Gmail or Outlook, and it parses them into a single master itinerary for your flights, hotels, and reservations. It's well established for that one job. Worth knowing: on Trustpilot, which reflects how a company treats its customers, TripIt sits at about 1.9, even though its iOS app rates higher. Pilot is a free trip planner rated 4.7 by 50,000+ travelers that does the same auto-import of your confirmations, adds a flexible planner you can shape yourself, and lets you book your stay in the app at private hotel rates, which TripIt can't do.
TripIt has a free tier that builds a master itinerary from the confirmations you forward in. Its more useful features sit behind TripIt Pro, which costs about $49 a year, including real-time flight alerts, gate and delay notifications, and seat tracking. Pilot is completely free, with no paywall on the basics: auto-import of your confirmations, a flexible drag-and-drop itinerary, a customizable map, AI itinerary generation, offline access, and PDF export are all included. Pilot can stay free because it earns from hotels when you book through the app, not from charging you to plan.
You forward travel confirmation emails to plans@tripit.com, or connect your Gmail or Outlook inbox, and TripIt parses each one and arranges it into a single chronological itinerary you can pull up on your phone. TripIt Pro adds flight alerts and other tracking for about $49 a year. The catch is that TripIt only organizes bookings you've already made somewhere else; it doesn't help you plan the trip and it doesn't book anything. Pilot does the same auto-import (forward a confirmation and Pilot scans it and suggests details to drop into your itinerary), then lets you actually build and reshape the plan with drag and drop, a customizable map, and AI, and book your stay in the app at private hotel rates.
TripIt earns from its TripIt Pro subscription, about $49 a year, and as part of Concur's broader travel and expense business. Pilot is free because it earns from hotels when you book through the app, not from charging you to plan, which is why the whole planner, including auto-import, offline access, and PDF export, stays free with no Pro tier.
No. TripIt organizes hotel bookings you've already made elsewhere by reading your confirmation emails, but it doesn't let you search or book hotels itself. Pilot lets you book over 3,000,000 hotels right in the app, with private deals straight from hotels, the kind usually reserved for travel agents, so the booking lives with the rest of your trip instead of on a separate site. Pilot lets you book hotels in the app; flights link out and aren't booked in Pilot.
TripIt is worth a look if all you want is a passive filing cabinet for confirmations you've booked elsewhere, and you don't mind paying about $49 a year for TripIt Pro to unlock flight alerts and seat tracking. But if you want to plan the trip, not just file it, Pilot does the same confirmation import for free, adds a flexible drag-and-drop planner, a customizable map, and AI itinerary generation, and lets you book your stay in the app at private hotel rates. So before paying for TripIt Pro, it's worth trying Pilot, which is free and does more.
Use Pilot if you want a free, flexible planner that's simple to use, auto-imports your confirmations, and also lets you book your stays at private hotel rates, all in one place, with real people to help when you need them. TripIt fits the narrow case where you only want a passive itinerary organizer for bookings you make elsewhere, you lean on its specific integrations like Apple Watch or Flighty sync, and you're happy to pay its $49 yearly Pro fee for flight alerts. For most people who want to plan and book, not just file an itinerary, Pilot does more for free.
Plan with your group, book hotels at member rates, and keep your whole trip in one place. Completely free.