Travel planning
You take the trip. Caddy takes the planning
The flight search. The booking emails. The airline check-in. Hand Caddy the travel tasks and spend a little more time looking forward to the trip.
Check me in for tomorrow’s United flight. Confirmation ABC123, last name Rivera
Ready to complete check-in: tomorrow at 9:20am, seat 18A, no checked bags or paid extras. Shall I finish?
Yes, finish check-in
You’re checked in for the 9:20am flight, seat 18A. Your boarding pass is ready.
The problem
Even a simple trip comes with a dozen jobs: compare flights, collect booking details, update your calendar, and work through airline check-in.
How Caddy helps
- Search flights for your dates and airports, compare the available fares, and find the lowest-priced options that fit.
- Find flight and hotel confirmations in Gmail and add the confirmed plans to Google Calendar.
- Work through airline check-in in the browser and retrieve your boarding pass after you approve the final step.
- Find a restaurant for the trip and work through its online reservation flow, checking any required choices or charges with you.
Why Caddy is different
You can delegate the next travel job in a text. Caddy works across search, your booking emails, and travel websites, then brings the result back to the same conversation.
Caddy in action
Find the flight and hotel confirmations for our Chicago trip in my email and add them to my calendar
Added both flights and the hotel check-in and checkout. The flight times use each airport’s local time, and the hotel events include the address.
What the workflow looks like
- 1
Text the job you want done, with your dates, airports, budget, or booking details.
- 2
Caddy searches the options or opens the relevant booking or check-in website.
- 3
Review the details when a purchase, invitation, or final airline check-in needs your approval.
- 4
Get the confirmed result, such as the events added to your calendar or your boarding pass.
Texts to try
- “Find the cheapest nonstop round-trip flight from JFK to LAX for October 16–20, for one adult in economy.”
- “Find our flight and hotel confirmation emails for Chicago and add them to my calendar.”
- “Check me in for tomorrow’s flight. I’ll send the airline, confirmation code, and last name.”
- “Book a table for two near our hotel Friday around 7. Somewhere with good vegetarian options.”
Common scenarios
Find a flight that fits
Give Caddy your airports, dates, and preferences. It compares returned fares and narrows the choices, so you can pick without working through all the tabs.
Turn booking emails into plans
Let Caddy find the confirmations and create calendar events with the right local times, addresses, and booking details.
Related: AI calendar assistant in iMessageGet checked in
Caddy can work through the airline website, ask you to review the final details, and retrieve the boarding pass when check-in succeeds.
Best ways to use it
- For flight searches, include dates, departure airports, passengers, and whether you want a round trip.
- Share the airline, confirmation code, and exact last name in the conversation when asking for check-in.
- Tell Caddy your seat and baggage preferences. It checks with you before changes or paid extras.
Frequently asked questions
Can Caddy find the cheapest flight?
Caddy can compare fares returned for your dates, airports, passengers, and cabin, then show the lowest-priced options that match. Prices and availability can change, and baggage or other extras may cost more.
Can Caddy check in for my flight?
Yes, when the airline’s website supports the flow. Share the airline, confirmation code, and exact last name in your conversation. Caddy works through check-in and asks before the final submission, seat changes, or extras. Some airlines require you to finish a login, verification, or check-in step yourself.
Does adding a trip to my calendar make a booking?
Adding a calendar event records the plan. A flight, hotel, or restaurant is booked only after the booking service confirms it. Caddy reviews any purchase with you before submitting it.
Can I start before I have booked anything?
Yes. Start with the trip you want and your dates or flexibility. Caddy can search flights and places, help you choose, and work through the next booking task.
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