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
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
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!
This site is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as thepointsguy.com. This may impact how and where links appear on this site. 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. Enrollment may be required for select American Express benefits and offers. Visit americanexpress.com to learn more. 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.
Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
IHG Kimpton Grand Cayman is a wonderful place to stay. The customer service there is outstanding! It is a bit further away from some restaurants, but you can catch a public “bus” (large vans) for $2.50 per person. You can find the bus routes and info online. We also stayed at the Westin and the location was within walking distance of many restaurants, but the customer service there was poor.
Another great thing to do is the bioluminescent tour. The color was amazing! Way better than what we saw in Jamaica! Be aware that the food is VERY expensive. We had a small breakfast at the “cheap place” across from Westin and it was $45! That was for orange juice, an omelet, and bacon for 2 people.
It was very nice and we do plan to return sometime.
Wow, that’s incredible for a “cheap” breakfast. We tend to eat at only off-site restaurants when staying at resorts, and we would have been shocked. Glad the Kimpton is so good, though!