Cheap Flights to Cayman Islands from $104 (2025/2026)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Cayman Islands's top cities

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.

Tue, Nov 11 - Tue, Nov 18
MIA
Miami Intl.
GCM
Owen Roberts Intl.
$309 Roundtrip, found 6 days ago
$309
Roundtrip
found 6 days ago
Select Cayman Airways flight, departing Tue, Nov 11 from Miami Intl. to Owen Roberts Intl., returning Tue, Nov 18, priced at $309 found 6 days ago
Sat, Oct 4 - Sat, Oct 11
JFK
John F. Kennedy Intl.
GCM
Owen Roberts Intl.
$312 Roundtrip, just found
$312
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Oct 4 from John F. Kennedy Intl. to Owen Roberts Intl., returning Sat, Oct 11, priced at $312 just found
Sat, Nov 15 - Sat, Nov 22
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$319 Roundtrip, found 2 hours ago
$319
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Sat, Nov 15 from Logan Intl. to Owen Roberts Intl., returning Sat, Nov 22, priced at $319 found 2 hours ago
Wed, Sep 10 - Tue, Sep 16
MIA
Miami Intl.
GCM
Owen Roberts Intl.
$325 Roundtrip, found 20 hours ago
$325
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Wed, Sep 10 from Miami Intl. to Owen Roberts Intl., returning Tue, Sep 16, priced at $325 found 20 hours ago
Tue, Nov 18 - Wed, Nov 19
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$330 Roundtrip, found 1 day ago
$330
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Nov 18 from Logan Intl. to Owen Roberts Intl., returning Wed, Nov 19, priced at $330 found 1 day ago
Sat, Dec 6 - Tue, Dec 9
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$338 Roundtrip, found 2 days ago
$338
Roundtrip
found 2 days ago
Select United flight, departing Sat, Dec 6 from Logan Intl. to Owen Roberts Intl., returning Tue, Dec 9, priced at $338 found 2 days ago
Sat, Sep 13 - Sat, Sep 20
MIA
Miami Intl.
CYB
Charles Kirkconnell Intl.
$348 Roundtrip, found 9 hours ago
$348
Roundtrip
found 9 hours ago
Select Cayman Airways flight, departing Sat, Sep 13 from Miami Intl. to Charles Kirkconnell Intl., returning Sat, Sep 20, priced at $348 found 9 hours ago
Thu, Sep 18 - Mon, Sep 22
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$360 Roundtrip, found 1 day ago
$360
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Sep 18 from Logan Intl. to Owen Roberts Intl., returning Mon, Sep 22, priced at $360 found 1 day ago
OriginDestinationTravel DatesFlights From*
YYZGeorge TownSeptember 27 to October 18$283
JFKGeorge TownOctober 4 to October 11$312
BOSGeorge TownNovember 15 to November 22$319
YULGeorge TownSeptember 26 to October 2$358
JFKLittle CaymanNovember 13 to November 16$411
ORDGeorge TownNovember 29 to December 6$414
JFKWest EndSeptember 8 to September 12$453
BOSLittle CaymanNovember 29 to December 5$710
ORDLittle CaymanSeptember 7 to September 18$740
LHRGeorge TownOctober 12 to October 23$952
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
LGAGeorge TownAugust 22 to August 27$348
JFKWest EndAugust 24 to September 5$578
YULGeorge TownAugust 24 to August 31$847
ORDGeorge TownAugust 22 to September 5$855
YYZGeorge TownAugust 22 to August 30$893
BOSGeorge TownAugust 23 to August 30$1,044
*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

Nov 2 - Nov 7

5 night stay

Boston (BOS) to George Town (GCM)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Hotel Indigo Grand Cayman by IHG
4.5-star property

Hotel Indigo Grand Cayman by IHG

Nov 2 - Nov 7

5 night stay

Boston (BOS) to George Town (GCM)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Cayman Luxury Rentals at Sunset Cove
3.5-star property

Cayman Luxury Rentals at Sunset Cove

Nov 2 - Nov 7

5 night stay

Boston (BOS) to George Town (GCM)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Boston to Cayman Islands
View all trips

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! (865 reviews)
"All the staff was very friendly"

Reviewed on Aug 16, 2025

Kimpton Seafire Resort + Spa by IHG
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! (1,001 reviews)
"It was a great stay. The only thing we disliked was the breakfast option, there was no buffet option during the weekdays."

Reviewed on Aug 12, 2025

Grand Cayman Marriott Resort
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! (1,003 reviews)
"Great staff and mr Raymond Wong and the concierge staff are amazing....they truly know their job"

Reviewed on Aug 17, 2025

The Ritz-Carlton, Grand Cayman
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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! (346 reviews)
"Having service everyone was friendly. Very clean."

Reviewed on Aug 16, 2025

Hotel Indigo Grand Cayman by IHG
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 November 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 $1,044. 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.