Waystop vs TripIt.
TripIt organizes what you’ve already booked. Forward the confirmation emails and you get one itinerary of flights, hotels and cars, with flight alerts if you pay for Pro. Waystop plans the part TripIt leaves blank: what to do all day. Ask Chat to plan a day and it comes back as one card, with stops in order, lunch and dinner, opening hours and the travel time between them. One tap adds it.
Free to plan every trip. $1.50 of Chat credit to start, no card needed.
Side by side
| What you need | TripIt | Waystop |
|---|---|---|
| Planning what to do | Not what it’s for | Ask Chat and the whole day comes back as one card you add with a tap |
| Opening hours and walks | — | Checked on Google Maps for the day you’re there |
| Getting bookings in | Forward emails or sync your inbox | Paste text, screenshots or PDFs into Import |
| Flight alerts | Delays, gates and cancellations with Pro | No |
| On the day | Your bookings in order | Leave-by times, the next stop on your lock screen, which train to take |
| Tickets and documents | In the itinerary | Attached to the stop, open offline |
| Money | — | A budget, plus “Sam paid for dinner” becomes who owes whom, in any currency |
| Packing and phrases | — | Packing lists, phrases and hand-off cards to show a local |
| Price | Free; Pro is a yearly subscription | Free to plan; Chat uses credit you add, no subscription |
TripIt details from its app listing and site, checked October 2026. Features change; check their site for the latest.
Which one to pick
You travel for work, your trips are mostly flights and hotels, and you want delay and gate alerts without lifting a finger. It’s the best at that.
The trip is the point and the days are still empty. Tell Chat what you’re into, get days with places that are actually open, and take the plan with you: when to leave, what the menu says, who owes whom.
Things you can ask Chat
Questions
Can I use both?
Yes, and plenty of people should. TripIt is great at flights and confirmations; Waystop plans what you do between them. Paste a confirmation or a screenshot into Waystop’s Import and it lands on the right day.
Does Waystop read my email like TripIt?
No. Waystop never connects to your inbox. You paste text, screenshots or PDFs of your bookings into Import and it builds the timeline from those.
Does Waystop have flight alerts?
No. If you fly often and want gate changes and delay alerts, that’s what TripIt Pro is for. Waystop keeps your bookings and tickets with the stop and opens them offline.
What does Waystop cost?
Free to plan every trip, with $1.50 of credit to try Chat, no card. After that, Chat, photo questions, web answers and imports use credit you add in the app, $5, $10 or $20 at a time. It never expires, and there’s no subscription.
Also see Waystop vs Wanderlog and how Waystop differs from planning in a chatbot.
Plan the days between the bookings.
Free to plan, no card needed. $1.50 of credit to try Chat, and an itinerary that’s yours to edit by hand for as long as you like.