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Tell Caddy your plans and it handles the rest

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Booked. It’s on your calendar now

Today9:41 AM
JFK to ORD, Oct 16–20. One adult, nonstop, under $350, there before 6pm.
Four nonstops fit. American at $278 is the cheapest and lands by 9:45am.

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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.

Top flights JFK to ORD on October 16: American $278, United $296, Delta $312, and American $334, round trip for one adult

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.

Today10:20 AM
Find a round trip JFK to ORD, Oct 16–20, one adult in economy. Nonstop, arriving before 6pm, under $350.
Four options fit. These are round-trip fares for one adult.
Caddy

Your questions, answered

Where are you flying?

Dates, destination, and what matters most. Start with a text.

AI flight finder in iMessage | Caddy