$110 Find Cheap Flights from New York to the Cayman Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New York to the Cayman Islands departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from New York to the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Townnonstop$319
Cayman Brac
Cayman Brac2 stops$1,005
George Town
George Townnonstop$319
Cayman Brac
Cayman Brac2 stops$1,005

Book Cheap New York to the Cayman Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New York to the Cayman Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from New York to the Cayman Islands

Sat, Aug 29 - Sat, Sep 5
United Airlines Logo
10:44 am - 1:35 pm
EWR
-
GCM
3h 51mnonstop
United Airlines Logo
2:45 pm - 7:30 pm
GCM
-
EWR
3h 45mnonstop
$319United Airlines
Sat, Aug 29 - Sat, Sep 5
United Airlines Logo
6:00 am - 12:25 pm
EWR
-
GCM
7h 25m
1 stop
United Airlines Logo
2:45 pm - 7:30 pm
GCM
-
EWR
3h 45mnonstop
$323United Airlines
Fri, Aug 28 - Tue, Sep 1
Delta Logo
6:00 am - 11:39 am
EWR
-
GCM
6h 39m
1 stop
Delta Logo
1:04 pm - 8:54 pm
GCM
-
EWR
6h 50m
1 stop
$333Delta
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
7:20 pm - 11:00 am
EWR
-
GCM
16h 40m
2 stops
American Airlines Logo
2:10 pm - 10:02 am
GCM
-
EWR
18h 52m
2 stops
$338American Airlines
Fri, Sep 4 - Tue, Sep 8
American Airlines Logo
6:00 am - 11:27 am
EWR
-
GCM
6h 27m
1 stop
American Airlines Logo
12:30 pm - 6:30 pm
GCM
-
EWR
29h 00m
1 stop
$340American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
6:30 pm - 11:00 am
EWR
-
GCM
17h 30m
1 stop
American Airlines Logo
4:00 pm - 9:59 am
GCM
-
EWR
16h 59m
1 stop
$342American Airlines
Wed, Oct 28 - Wed, Nov 4
American Airlines Logo
5:45 pm - 10:45 am
EWR
-
GCM
18h 00m
2 stops
American Airlines Logo
9:00 am - 10:29 pm
GCM
-
EWR
13h 29m
2 stops
$343American Airlines
Mon, Aug 31 - Sun, Sep 6
Cayman Airways Logo
11:45 am - 2:45 pm
JFK
-
GCM
4h 00mnonstop
Cayman Airways Logo
6:10 pm - 11:00 pm
GCM
-
JFK
3h 50mnonstop
$368Cayman Airways
Wed, Jul 22 - Sun, Jul 26
Multiple Airlines Logo
8:45 am - 3:25 pm
LGA
-
CYB
31h 40m
2 stops
Multiple Airlines Logo
6:20 pm - 10:35 pm
CYB
-
LGA
27h 15m
2 stops
$1,005Multiple Airlines
Wed, Jul 22 - Sun, Jul 26
Multiple Airlines Logo
7:55 pm - 3:25 pm
LGA
-
CYB
20h 30m
2 stops
Multiple Airlines Logo
6:20 pm - 10:35 pm
CYB
-
LGA
27h 15m
2 stops
$1,038Multiple Airlines
Booking Insights

KAYAK's insights & trends for New York to the Cayman Islands flights

Get data-powered insights and trends into flights from New York to the Cayman Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest New York to the Cayman Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to the Cayman Islands from New York found in the last 5 days was to George Town, at $305 round-trip. The most popular route is from New York John F Kennedy Intl Airport (JFK) to George Town (GCM), and the cheapest round-trip airline ticket found on this route in the last 5 days was $305.

What is the cheapest time of day to fly to the Cayman Islands?

The average price for all round-trip flights from New York to the Cayman Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to the Cayman Islands is generally in the evening, when round-trip flights cost $343 on average. Morning departures are around 24% more expensive than evening flights, on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $426.

Can I save money by flying with a layover from New York to the Cayman Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $530, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from New York to the Cayman Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from New York to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from New York to the Cayman Islands is November, when tickets cost $99 (return) on average. On the other hand, the most expensive months are March and January, when the average cost of round-trip tickets is $1,338 and $1,168 respectively.

What’s the cheapest day of the week to fly from New York to Cayman Islands?

The average price of all round-trip flights from New York to the Cayman Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Cayman Islands on a Wednesday and more expensive on a Tuesday. On your return trip to New York, you should consider flying back on a Tuesday, and avoid Fridays for better deals.

How far in advance should I book a flight from New York to the Cayman Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from New York to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from New York to the Cayman Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$110
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from New York John F Kennedy Airport to George Town

FAQs - booking Cayman Islands flights

  • What type of documentation will I need to make a flight to the Cayman Islands?

    Citizens of the United States making the trip to the Cayman Islands need to have a valid passport when they arrive in the country. For those traveling on a vacation to this beautiful destination as a tourist, there is no need to obtain any type of visa to make a trip to the Cayman Islands.

  • If I plan on renting a car when I arrive in the Cayman Islands, what child car seat laws do I need to know about?

    Laws in this country state that any child traveling any vehicle needs to be wearing a seatbelt. Any child that is under the age of 14 years old needs to ride in the rear of a vehicle. Any child traveling in a rear-facing child car seat cannot ride in a seat with a front airbag. All children two years old and younger need to be in a proper child restraint seat. Confirm with your rental car company that they can rent you car seats if you do not plan on bringing your own.

  • Are there any public transportation options to get me from the center of Newark to Newark International Airport?

    One of the most convenient ways to get to this airport is the travel aboard NJ Transit trains making the trip to the Newark Liberty Airport Station. Once at the station, you can hop aboard the Air Train that offers service to all of the terminal buildings at the airport.

  • Are there any lounges where I can wait for my flight to the Cayman Islands at New York La Guardia Aiport?

    This airport offers lounges from American Airlines, United Airlines, and Delta Airlines. There is also a Centurion Lounge as well as a Minute Suites express location inside the airport terminal buildings.

  • How does KAYAK find such low prices on flights from New York to the Cayman Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New York to the Cayman Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New York to the Cayman Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from New York to the Cayman Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from New York to the Cayman Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from New York to the Cayman Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New York to the Cayman Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from New York to the Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to the Cayman Islands

  • If you are traveling from the New York area to the small island airport of Little Cayman (LYB), you will find two-stop flights departing from both Newark International Airport (EWR) and New York La Guardia Aiport (LGA).
  • For travelers looking for a convenient way to New York La Guardia Aiport without having to drive, a quick and convenient choice is to ride aboard the LaGuardia Link Q70 bus. This bus offers service from neighborhoods like Queens, Manhattan, and Long Island to the airport.
  • If you're looking for a very comfortable place to wait for your Newark International Airport flight to the Cayman Islands, this airport has airline lounges from Lufthansa airlines, United Airlines, American Airlines, British Airways, and Delta Airlines.
  • If you are looking for a quick and convenient way to get from George Town Owen Roberts International Airport (GCM) to the center of George Town, consider riding aboard the line number five bus operated by Grand Cayman Island Buses that makes the trip in around 9min.
  • If you have traveled all the way to the George Town Owen Roberts International Airport and forgot to do a currency exchange before you departed from the New York area, this Airport offers currency exchange services and even has an auto-exchange machine in the terminal building.

Reviews of the top 5 airlines serving from New York to the Cayman Islands

 
Need help choosing which airline to fly with from New York to the Cayman Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
9.0
Cayman AirwaysOverall score based on 33 reviews
9.5Crew
8.6Comfort
6.3Food
9.0Boarding
7.2Entertainment
Airline reviews

Flight departed early and arrived early. Excellent, orderly boarding, ample legroom. Great crew and a very smooth flight.

10.0 ExcellentJeffrey, Apr 2026
GCM - MIA
Read more Cayman Airways reviews

Flight departed early and arrived early. Excellent, orderly boarding, ample legroom. Great crew and a very smooth flight.

There is no food or entertainment in this flight. Service was excellent.

Short flight. Excellent boarding and crew. Flight left early and arrived early!

Great flight on the Twin Otter. Early departure and early arrival. Hassle free flight.

Boarded 20 minutes late, dinner and beverages were provided but the "main" of dinner was freezing cold and had soggy lettuce. The seats were wildly uncomfortable! There was in-flight entertainment that you can access via your phone (vs. the TV on the seatback in front of you) but the wifi connection was weak and you could not actually play anything. With that said, the crew was very pleasant and friendly!

Flight crew made the flight very enjoyable as they were friendly, helpful and accommodating. Flight time was 3:40 compared to the 4:30 that was captured on our itinerary, so that was a pleasant surprise. In flight entertainment was good with plenty of selection, however some of the choices that my family tried were slow to load and stalled out a few times. We were able to restart and everyone finished watching their movies. Food was pretty basic: croissant, turkey or chicken lunch meat with Swiss cheese and a bag of Lay’s potato chips. Still a bonus considering most airlines offerings which is nothing but peanuts or a cookie.

Best experience ever. Crew were amazing, kept me informed throughout. Boarding was on time and spot on. Id book again most def

Food could have been better, and internet that allows texting/WhatsApp and other basics on the phone instead of just inflight entertainment would have been nice.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

I'm a United 1K member and have ben for 10 years. The gate agent had no control over the boarding process and had us passengers queued for hours as delays were announced. On the plane, the overhead air nozzle was broken so col over was powering through on me and the passenger next to me. Not a great experience for a million miler on United. Feel free to contact me. Josh Smigel - DM426089

Everything was the best it could be. Crew found me with pre- ordered food. Excellent experience!

Improve the food offerings and cabin seating. My wife would prefer to fly another airline, even with a connection for a more comfortable trip. A 737-8 should not be scheduled for a 6 hour segment, which turned into 7.5 hours due to the origin ground delay.

Check in was chaotic with only one counter for business class and first class. The luggage conveyor belt at JFK airport was broken so the flight departure was delayed which made the flight stressful as I had a tight connection. Although the captain said they could make up the delay, they didn’t do so.

As I wrote earlier, poor planning and/or communication. At least twice, we were told that we would be boarding in less than ten minutes, only to have the flight again delayed at least another hour.

Cree was organized and pleasant. Plane had good seating but as it’s a shuttle toilets hadn’t been thoroughly cleaned (eg. bins too full)

All good flight was 35 minutes early when arriving in Edinburgh

Flight left on time, arrived early, pleasant staff provided water, coffee, etc. access to bathrooms was reasonable and were well maintained. blankets were available, lots of entertainment options. LUGGAGE SERVICE WAS GREAT. I got my one checked bag quickly and was able to make a bus connection for a 2 hour bus ride saving me from waiting another 1.5 hours.

I had a good time. However, I paid for the wifi and it was in and out the whole flight.

They promise free wi-fi prior to boarding and then once on board you are informed you have to purchase wifi even after being a mileagePlus member.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

The flight attendant on my side of business class seemed like a novice and did not provide good service. Otherwise the flight was good and the entertainment system was very good. No free WiFi.

Flying in the United States with the major airlines has become so underwhelming. A 2-3hr flight in most other parts of the world with the major carriers of the area comes with newer, CLEANER aircraft and significantly better in flight service in terms of both staff attitude and a actual meal service.

I am writing to share detailed feedback regarding my recent journey with American Airlines on the New York (JFK) to New Delhi (DEL) sector, which was ultimately diverted to Jaipur (JAI) due to weather conditions. At the outset, I would like to acknowledge that this was a full long-haul flight of approximately 14–15 hours, and while the journey fulfilled its primary transport objective, several aspects of the experience warrant both recognition and constructive feedback. 1. Cabin Crew Conduct and Service Consistency While the majority of the cabin crew maintained a polite and professional demeanor, one flight attendant’s conduct was notably inconsistent with expected service standards. The tone was often directive and lacked the warmth and guest-centric engagement typically associated with long-haul service. This created a perceptible imbalance in the cabin experience. Although other crew members acknowledged and apologized for the behavior, it highlighted a gap in service standardization and supervisory oversight. 2. Inflight Experience (IFE & Comfort) The inflight entertainment system was unreliable, with content failing to load consistently throughout the journey. Seating comfort in economy class was below expectations when compared with other international long-haul carriers. Cabin environment management at times felt unsettled, with noticeable noise and movement in the aisles. 3. Disruption Handling and Communication (DEL Diversion to JAI) The diversion to Jaipur due to weather was understandably beyond the airline’s control. However, the handling of post-diversion communication and guest management was an area of concern: Information during and after the diversion was fragmented and lacked clarity Limited guidance was provided upon disembarkation regarding next steps (transport, accommodation, onward travel) Ground coordination appeared inconsistent, with hotel partners and passengers receiving incomplete or delayed updates Communication the following morning remained unclear, including last-minute changes to transfer timings This resulted in avoidable uncertainty during a critical disruption phase. 4. Positive Acknowledgment – Ground Recovery Arrangements It is important to recognize that despite the initial communication gaps, the overall recovery framework was eventually well executed: Hotel accommodation was arranged efficiently Meal vouchers were provided appropriately Transfers between airport and hotel were organized in a structured manner Given the sudden and large-scale disruption, these arrangements were commendable and reflect the airline’s ability to operationally recover once systems were in place. 5. Recommendations for Improvement In the interest of strengthening the overall customer experience, I would respectfully propose the following: Service Delivery Reinforce consistent cabin crew service standards, particularly for long-haul sectors Enhance supervisory presence to address outlier behaviors in real time Inflight Product Improve reliability of inflight entertainment systems Reassess economy seating comfort for ultra-long-haul routes Disruption Management Establish a more visible “Care & Coordination Team” during irregular operations Ensure clear, centralized communication (single source of truth) for passengers and ground partners Provide structured briefing points to hotel and transport vendors to avoid information gaps Introduce proactive guest engagement (clear next steps, timelines, reassurance) Closing Reflection: While the journey was impacted by both controllable and uncontrollable factors, the overall experience would have been significantly enhanced through greater consistency in service delivery and more structured communication during disruption. I appreciate the efforts made by the broader team in arranging accommodation and onward logistics under challenging circumstances. With improved coordination and alignment, the experience can be elevated to match the expectations of a global long-haul carrier. Thank you for your attention to this feedback. I trust it will be received constructively and contribute to ongoing service improvement. Warm regards, Soosnata Chowdhury Convert effective for airlines) Or tailor tone

Wifi was spotty. Tray table was very dirty when I sat down.

Flight was extremely hot and they made us check our bags when the space was nowhere near full

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

For an international flight the seats were smaller than most flight I have been on in economy. I don’t know the size of the seats or perhaps it was the size of the seat dividers that made the seats feel smaller and little amount of space to even turn your body if you needed to

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

First the flt was delayed over 2 hrs bc of plane mechanics that should have been handled better! No text or email was sent so only found out at the airport so there we sat for 5 hours! THATS RIDICULOUS! The gate area was filthy! No agents showed up till hr before so no additional info was given-waited online for 15 mins while the gate agent chatted and got together then given last seat in back of plane!! No priority for senior or anything-took attendants over 2hrs to serve drinks and snack-WHY are they not served together? By time snack came needed another drink! Worst service in my life!

All the TV screens in my rows was non functional . The map shown for an international route was antiqued..

Boarding process was terrible. No assigned seat until the gate, then a long line to get seat assignment.

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

Everything you need to know for your flight from New York to the Cayman Islands

Cabin class types available on flights to the Cayman Islands

Cabin classes available on flights to the Cayman Islands. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.