Your new travel agent
Tell Caddy your plans and it handles the rest



Booked. It’s on your calendar now







An illustrative conversation with Caddy in iMessage
A little less searching. A little closer to going.

Land by 6pm
JFK → ORD · Nonstop · Under $350
Search with your real-life constraints
Need to arrive before dinner or fly from one particular airport? Tell Caddy up front so it can look for options that fit your actual plans.



Compare the tradeoffs at a glance
See fares, departure and arrival times, stops, and travel time together. Weigh the lower price against the flight that makes your day easier.

Booked on American
$278 round trip · Oct 16–20 · Approved before paying
Say “book it” and it’s done
Pick your outbound and return. Caddy books the trip and checks with you before paying.
Start with the flight that fits your day
Give Caddy the airports, dates, and what matters: a lower fare, a shorter travel day, or landing in time for dinner. It compares what it finds and sends the options.



Your questions, answered

Where are you flying?
Dates, destination, and what matters most. Start with a text.