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Hand-picked deals by our pirate teamGet inspired!Hand-picked deals by our pirate team
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Hand-picked deals by our pirate teamGet inspired!Hand-picked deals by our pirate team
Rays in the Cayman Islands
This deal is already a few days old and availability may have changed.
Flights

Cheapest Flights We've Ever Seen to the Cayman Islands 🏝️😮

Fly to the Cayman Islands from $183 Round Trip — Usually $600+

From $183

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Published by
Molly Cowen·11/11/2025
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Pirates, we've found incredible rates on flights to the Cayman Islands from $183 round trip! In fact, these are the cheapest flights we've ever seen. Usually, you'd pay over $600, so these flights will save you over 60% off. This deal includes nationwide US and Canadian departures, with the best deals on winter and spring dates through May.

Highlights

Close to the Beach
Great for Couples
Great for Groups
Top Location

Departure

  • Boston
  • New York City
  • Austin
  • Los Angeles
  • New Orleans
  • Dallas
  • Toronto
  • Houston
  • Montreal
  • Chicago

Destination

  • Grand Cayman
  • Caribbean

Other Options

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Additional Information

All of our deals are available at the time of publishing, but prices are subject to fluctuate and change at any time.

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