Cheap Flights to Cayman Islands from $109 (2026/2027)

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Jet to one of Cayman Islands's top cities

A coastal city with a beach, clear blue waters, and a distant ship.

Seven Mile Beach

Flights
Seven Mile Beach

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.

Thu, Nov 12 - Sun, Nov 15
MIA
Miami Intl.
GCM
Owen Roberts Intl.
$287 Roundtrip, just found
$287
Roundtrip
just found
Select Cayman Airways flight, departing Thu, Nov 12 from Miami Intl. to Owen Roberts Intl., returning Sun, Nov 15, priced at $287 just found
Thu, Dec 17 - Sun, Dec 20
MIA
Miami Intl.
GCM
Owen Roberts Intl.
$292 Roundtrip, found 6 hours ago
$292
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Thu, Dec 17 from Miami Intl. to Owen Roberts Intl., returning Sun, Dec 20, priced at $292 found 6 hours ago
Sat, Apr 17 - Sat, Apr 24
MIA
Miami Intl.
CYB
Charles Kirkconnell Intl.
$339 Roundtrip, found 3 hours ago
$339
Roundtrip
found 3 hours ago
Select Cayman Airways flight, departing Sat, Apr 17 from Miami Intl. to Charles Kirkconnell Intl., returning Sat, Apr 24, priced at $339 found 3 hours ago
Wed, Oct 21 - Sun, Oct 25
EWR
Newark Liberty Intl. Airport
GCM
Owen Roberts Intl.
$340 Roundtrip, found 3 days ago
$340
Roundtrip
found 3 days ago
Select Air Canada flight, departing Wed, Oct 21 from Newark Liberty Intl. Airport to Owen Roberts Intl., returning Sun, Oct 25, priced at $340 found 3 days ago
Fri, Oct 23 - Fri, Oct 30
LGA
LaGuardia
GCM
Owen Roberts Intl.
$346 Roundtrip, found 2 days ago
$346
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, Oct 23 from LaGuardia to Owen Roberts Intl., returning Fri, Oct 30, priced at $346 found 2 days ago
Sat, Oct 24 - Wed, Oct 28
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$346 Roundtrip, just found
$346
Roundtrip
just found
Select Air Canada flight, departing Sat, Oct 24 from Logan Intl. to Owen Roberts Intl., returning Wed, Oct 28, priced at $346 just found
Wed, Oct 21 - Sun, Nov 1
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$346 Roundtrip, found 7 hours ago
$346
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Wed, Oct 21 from O'Hare Intl. to Owen Roberts Intl., returning Sun, Nov 1, priced at $346 found 7 hours ago
Sat, Nov 28 - Sat, Dec 5
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$373 Roundtrip, found 4 hours ago
$373
Roundtrip
found 4 hours ago
Select United flight, departing Sat, Nov 28 from Logan Intl. to Owen Roberts Intl., returning Sat, Dec 5, priced at $373 found 4 hours ago
OriginDestinationTravel DatesFlights From*
YYZGeorge TownSeptember 5 to September 12$289
YULGeorge TownSeptember 18 to September 28$317
BOSGeorge TownOctober 18 to October 22$346
ORDGeorge TownOctober 16 to October 24$346
EWRGeorge TownOctober 18 to October 24$346
JFKWest EndSeptember 21 to September 27$467
LHRGeorge TownSeptember 5 to September 12$1,092
JFKLittle CaymanSeptember 1 to September 6$3,032
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
YYZGeorge TownAugust 14 to August 24$479
LGAGeorge TownAugust 15 to August 22$620
BOSGeorge TownAugust 16 to August 22$1,136
LHRGeorge TownAugust 14 to August 22$1,799
*Prices include taxes and fees

Best Cayman Islands Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Reef Beach Resort, East End, Grand Cayman
3.5-star property

The Reef Beach Resort, East End, Grand Cayman

Sep 28 - Oct 5

7 night stay

Boston (BOS) to George Town (GCM)

American Airlines • Non-stop • Coach

George Town (GCM) to Boston (BOS)

Air Canada • Non-stop • Coach
Price was $1,899, price is now $1,020 per person
$1,020
per person
found 1 day ago
Black Urchin
4.5-star property

Black Urchin

Oct 26 - Oct 30

4 night stay

Boston (BOS) to George Town (GCM)

American Airlines • Non-stop • Coach

George Town (GCM) to Boston (BOS)

Air Canada • Non-stop • Coach
Price was $6,498, price is now $3,850 per person
$3,850
per person
found 1 day ago
Point West Premier Rentals
4.0-star property

Point West Premier Rentals

Sep 28 - Oct 5

7 night stay

Boston (BOS) to George Town (GCM)

American Airlines • Non-stop • Coach

George Town (GCM) to Boston (BOS)

Air Canada • Non-stop • Coach
Price was $1,926, price is now $1,261 per person
$1,261
per person
found 1 day ago
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Travelers ❤️ These Cayman Islands 🏨

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
Book a stay at this luxury hotel in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 4 restaurants. Popular attractions Seven Mile Beach and Governor's Beach are located nearby.
Opens in a new windowHotel Indigo Grand Cayman by IHG
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
West Bay Road Seven Mile Beach Grand Cayman
Book a stay at this luxury resort in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Governor's Beach and Seven Mile Beach are located nearby.
Opens in a new windowThe Ritz-Carlton, Grand Cayman
Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way Seven Mile Beach Grand Cayman
Book a stay at this 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 Governor's Beach are located nearby.
Opens in a new windowKimpton Seafire Resort + Spa by IHG
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The Locale Hotel Grand Cayman

The Locale Hotel Grand Cayman

3.5 out of 5
455 West Bay Road Seven Mile Beach Grand Cayman
Book a stay at this business-friendly hotel in Seven Mile Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Governor's Beach and Port of Georgetown are located nearby.
9.4/10 Exceptional! (1,015 reviews)
"Great place to stay. Staff was very helpful. Cleaners throughout the hotels cleaning frequently. Free breakfast. Great for solo travels or family’s."

Reviewed on Aug 9, 2026

Opens in a new windowThe Locale Hotel Grand Cayman
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 $287. 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. $287 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 $287 and $3,032. 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.

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