Please ensure Javascript is enabled for purposes of website accessibility

I have a friend at the Grand Cayman Marriott Beach Resort right now, and the pictures she keeps posting are making me jealous. The water is so blue and clear that I’m pre-planning a 2020 trip. If you’d like to go this year, JetBlue has good fares from several cities to Grand Cayman this fall and through to next February. The New York flights sometimes include Delta or American, and both are matching JetBlue’s pricing on some dates from that city. While “not summer” might seem odd for a Caribbean vacation, the temperature remains great year round, though it’s rainy/storm season at times in the fall so be aware.

  • New York from $302
  • Chicago from $344
  • Phoenix from $371
a swimming pool with a jacuzzi and palm trees

Grand Cayman resort by Pixabay user james3214

These are “Blue” fares, which are their basic economy. That includes carry-on, seat choice, meals, and wi-fi/broadband. These can be booked direct with the airline or with OTAs, but direct booking sometimes requires separate tickets. The Chicago and Phoenix fares are available only for select dates, so if you’re looking for a Grand Cayman trip book sooner rather than later.

Sample Route

  • Departure: New York JFK
  • Stops: None
  • Arrival: Georgetown Grand Cayman

a screenshot of a website

How to Book

  • Follow link for sample dates or search your favorite OTA / Google Flights for departure and destination

Travel Dates

  • September 2019 through February 2020
  • 7-day stay required

Where to Stay on Grand Cayman

Things to Do on Grand Cayman

Good luck and happy flying!

Points With a Crew has partnered with CardRatings for our coverage of credit card products. Points With a Crew and CardRatings may receive a commission from card issuers. Responses are not provided or commissioned by the bank advertiser. Some or all of the card offers that appear on the website are from advertisers and that compensation may impact on how and where card products appear on the site. Any opinions expressed in this post are my own, and have not been reviewed, approved, or endorsed by my advertising partners and I do not include all card companies, or all available card offers. Terms apply to American Express benefits and offers and other offers and benefits listed on this page. Other links on this page may also pay me a commission - as always, thanks for your support if you use them

User Generated Content Disclosure: Points With a Crew encourages constructive discussions, comments, and questions. Responses are not provided by or commissioned by any bank advertisers. These responses have not been reviewed, approved, or endorsed by the bank advertiser. It is not the responsibility of the bank advertiser to respond to comments.