Cheap Flights to Cayman Islands from $107 (2025/2026)

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Seven Mile Beach

Flights
Seven Mile Beach

West Bay

Flights
West Bay

How Much Does it Cost To Fly To Cayman Islands?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Oct 18 - Sun, Oct 26
JFK
John F. Kennedy Intl.
GCM
Owen Roberts Intl.
$307 Roundtrip, found 2 days ago
$307
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Oct 18 from John F. Kennedy Intl. to Owen Roberts Intl., returning Sun, Oct 26, priced at $307 found 2 days ago
Mon, Oct 20 - Sun, Oct 26
EWR
Newark Liberty Intl. Airport
GCM
Owen Roberts Intl.
$315 Roundtrip, found 2 days ago
$315
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Oct 20 from Newark Liberty Intl. Airport to Owen Roberts Intl., returning Sun, Oct 26, priced at $315 found 2 days ago
Sat, Nov 15 - Sat, Nov 22
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$316 Roundtrip, found 9 hours ago
$316
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Sat, Nov 15 from Logan Intl. to Owen Roberts Intl., returning Sat, Nov 22, priced at $316 found 9 hours ago
Thu, Dec 4 - Thu, Dec 11
TPA
Tampa Intl.
GCM
Owen Roberts Intl.
$317 Roundtrip, found 15 hours ago
$317
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Thu, Dec 4 from Tampa Intl. to Owen Roberts Intl., returning Thu, Dec 11, priced at $317 found 15 hours ago
Wed, Dec 3 - Sat, Dec 6
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$319 Roundtrip, found 4 days ago
$319
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Dec 3 from O'Hare Intl. to Owen Roberts Intl., returning Sat, Dec 6, priced at $319 found 4 days ago
Wed, Nov 26 - Sun, Nov 30
MIA
Miami Intl.
GCM
Owen Roberts Intl.
$325 Roundtrip, just found
$325
Roundtrip
just found
Select Cayman Airways flight, departing Wed, Nov 26 from Miami Intl. to Owen Roberts Intl., returning Sun, Nov 30, priced at $325 just found
Wed, Oct 22 - Wed, Oct 29
LGA
LaGuardia
GCM
Owen Roberts Intl.
$336 Roundtrip, found 5 days ago
$336
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Oct 22 from LaGuardia to Owen Roberts Intl., returning Wed, Oct 29, priced at $336 found 5 days ago
Sat, Sep 13 - Sat, Sep 20
MIA
Miami Intl.
CYB
Charles Kirkconnell Intl.
$348 Roundtrip, found 4 days ago
$348
Roundtrip
found 4 days ago
Select Cayman Airways flight, departing Sat, Sep 13 from Miami Intl. to Charles Kirkconnell Intl., returning Sat, Sep 20, priced at $348 found 4 days ago
OriginDestinationTravel DatesFlights From*
YYZGeorge TownSeptember 13 to September 20$283
JFKGeorge TownOctober 27 to November 3$308
BOSGeorge TownNovember 15 to November 22$316
ORDGeorge TownDecember 3 to December 6$319
YULGeorge TownSeptember 8 to September 14$365
JFKLittle CaymanSeptember 8 to September 12$477
JFKWest EndSeptember 8 to September 12$483
BOSLittle CaymanDecember 4 to December 12$858
LHRGeorge TownOctober 12 to October 23$952
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
YYZGeorge TownAugust 30 to September 6$336
EWRGeorge TownAugust 30 to September 6$339
BOSGeorge TownAugust 29 to August 31$617
ORDGeorge TownAugust 31 to September 19$785
*Prices include taxes and fees

Best Cayman Islands Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Reef Resort Grand Cayman
3.5-star property

Wyndham Reef Resort Grand Cayman

Oct 31 - Nov 5

5 night stay

Boston (BOS) to George Town (GCM)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,476, price is now $944 per person
$944
per person
found 1 day ago
Hotel Indigo Grand Cayman by IHG
4.5-star property

Hotel Indigo Grand Cayman by IHG

Oct 31 - Nov 5

5 night stay

Boston (BOS) to George Town (GCM)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,075, price is now $1,238 per person
$1,238
per person
found 1 day ago
Kimpton Seafire Resort + Spa by IHG
5.0-star property

Kimpton Seafire Resort + Spa by IHG

Oct 1 - Oct 5

4 night stay

Boston (BOS) to George Town (GCM)

American Airlines • Non-stop • Coach

George Town (GCM) to Boston (BOS)

United • Non-stop • Coach
Save 100% on your flight
Price was $1,659, price is now $1,052 per person
$1,052
per person
found 1 day ago
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Travelers ❤️ These Cayman Islands 🏨

Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way, Seven Mile Beach, Grand Cayman
Stay at this 5-star luxury hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
9.8/10 Exceptional! (874 reviews)
Fantastic stay
"Another lovely stay. The accommodations, resort, the people - all top notch. Highly recommend."

Reviewed on Aug 22, 2025

Kimpton Seafire Resort + Spa by IHG
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
32 Seafire Way, Seven Mile Beach, West Bay
Stay at this 4.5-star luxury hotel in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 4 restaurants. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
9.6/10 Exceptional! (356 reviews)
"Staff was super attentive in all areas…check-in, pool, dining, valet, beach. Very clean and easy access to beach and area attractions"

Reviewed on Aug 23, 2025

Hotel Indigo Grand Cayman by IHG
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
West Bay Road, PO Box 32348 KY1-1209, Seven Mile Beach, Grand Cayman
Stay at this 5-star luxury resort in Seven Mile Beach. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
9.4/10 Exceptional! (1,002 reviews)
"One of mostly stylish and friendly location at Caribian , super nice and friendly staff , clean , absolutely gorgeous beach area , very rear hotel restaurant making good food this one doing very well in all l levels starting from breakfast and till dinner , absolutely not expecting such great ..."

Reviewed on Aug 20, 2025

The Ritz-Carlton, Grand Cayman
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Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
389 West Bay Road, Po Box 30371, Seven Mile Beach, Grand Cayman
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of Georgetown and Seven Mile Beach are located nearby.
8.8/10 Excellent! (1,002 reviews)
"Very clean and beautiful"

Reviewed on Aug 23, 2025

Grand Cayman Marriott Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Cayman Islands?
Your next trip doesn't have to make a huge dent in your finances. In the last seven days, the cheapest return flight to Cayman Islands cost $283. Find a bargain fare and spend the dollars you save on exciting experiences. This price was available on Travelocity for flights to Cayman Islands departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Cayman Islands?
Find your perfect fare with one of the 15 airlines that operate flights to Cayman Islands. If you're staying in George Town, let Cayman Airways take you to this dynamic city to enjoy its iconic attractions. This popular carrier offers 385 flights there per month.
What is the cheapest month to fly to Cayman Islands?
Make sure you leave October clear in your calendar, because it's the most affordable month to jet out to Cayman Islands. That's based on Travelocity's direct flight demand from January to December last year. With more money in your wallet, you can splurge on a hotel upgrade, go to a fancy restaurant or whatever else you feel like!
How can I check my flight status to Cayman Islands?
Get updates about your flight status, any gate changes and more with Trips. This handy customer portal can be found at the top right of our homepage and is where you can view and manage your bookings. Create an account in just a few seconds and you're all set. You can also use the Travelocity app to look up the details of your flight to Cayman Islands while you're on the move — and even when you're offline. Travelocity's app is the travel companion in your pocket. Whether you want to organize transportation from your airport or share itinerary details with any members of your family flying with you, the app is your one-stop shop.
How do I find the best deals on flights to Cayman Islands?
Score an amazing deal with Travelocity — our "Flexible dates" function makes it that much easier. Enter your travel dates, then hit the flexible dates box above your search results to see the prices for surrounding days. $283 was the best price for a return flight to Cayman Islands in the last seven days. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Cayman Islands with Travelocity?
A memorable vacation is at your fingertips when you book with Travelocity. With a wide selection of choices and great deals on cheap family flights, rental cars and more, we make it easy to find awesome prices to suit your needs. You can also make use of our 24/7 customer support and free cancellation policies on most hotels during every step of the process. Wander wisely with us and bag your cheap flights to Cayman Islands today.
What are the most popular flight routes to Cayman Islands?
To help you pick your flights to Cayman Islands, here's our list of some of the main routes:

  • West End (CYB-Gerrard Smith Intl.) to Owen Roberts Intl. Airport (GCM) - 693 flights a month.
  • Little Cayman (LYB-Edward Bodden Airfield) to Owen Roberts Intl. Airport (GCM) - 407 flights a month.
  • Miami, FL (MIA-Miami Intl.) to Owen Roberts Intl. Airport (GCM) - 221 flights a month.

How much is a flight to Cayman Islands on average?
In the last seven days, roundtrip flights to Cayman Islands were priced between $283 and $952. No matter what sort of ticket you're after, we have some amazing deals to help you keep to your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Cayman Islands?
Listed here are a selection of leading direct flights to Cayman Islands along with their average journey times:

  • West End (CYB-Gerrard Smith Intl.) to Owen Roberts Intl. Airport (GCM) - 39 minutes
  • Little Cayman (LYB-Edward Bodden Airfield) to Owen Roberts Intl. Airport (GCM) - 35 minutes
  • Miami, FL (MIA-Miami Intl.) to Owen Roberts Intl. Airport (GCM) - 1 hour and 29 minutes

What can I expect on a flight to Cayman Islands?
This mostly depends on where you're setting off from and which airline you choose. You're likely to find all types of flights to Cayman Islands, from premium fares to cheap flights for family vacations. For long-haul flights, airlines will typically provide hot meals and entertainment as well as games for your little ones.

Destinations in Cayman Islands

Top Flight Routes

Top Airlines

Top Airports

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.