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

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

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, Oct 22 - Sun, Oct 25
MIA
Miami Intl.
GCM
Owen Roberts Intl.
$287 Roundtrip, just found
$287
Roundtrip
just found
Select Cayman Airways flight, departing Thu, Oct 22 from Miami Intl. to Owen Roberts Intl., returning Sun, Oct 25, priced at $287 just found
Fri, Oct 9 - Sun, Oct 25
MIA
Miami Intl.
GCM
Owen Roberts Intl.
$292 Roundtrip, found 5 days ago
$292
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Oct 9 from Miami Intl. to Owen Roberts Intl., returning Sun, Oct 25, priced at $292 found 5 days ago
Mon, Oct 12 - Sun, Oct 18
JFK
John F. Kennedy Intl.
GCM
Owen Roberts Intl.
$331 Roundtrip, found 1 day ago
$331
Roundtrip
found 1 day ago
Select Cayman Airways flight, departing Mon, Oct 12 from John F. Kennedy Intl. to Owen Roberts Intl., returning Sun, Oct 18, priced at $331 found 1 day ago
Sat, Jun 5 - Sat, Jun 12
MIA
Miami Intl.
CYB
Charles Kirkconnell Intl.
$356 Roundtrip, found 1 day ago
$356
Roundtrip
found 1 day ago
Select Cayman Airways flight, departing Sat, Jun 5 from Miami Intl. to Charles Kirkconnell Intl., returning Sat, Jun 12, priced at $356 found 1 day ago
Thu, Sep 10 - Mon, Sep 14
MIA
Miami Intl.
LYB
Edward Bodden Airfield
$394 Roundtrip, found 2 days ago
$394
Roundtrip
found 2 days ago
Select Cayman Airways flight, departing Thu, Sep 10 from Miami Intl. to Edward Bodden Airfield, returning Mon, Sep 14, priced at $394 found 2 days ago
Sat, Mar 20 - Thu, Mar 25
TPA
Tampa Intl.
GCM
Owen Roberts Intl.
$397 Roundtrip, just found
$397
Roundtrip
just found
Select Cayman Airways flight, departing Sat, Mar 20 from Tampa Intl. to Owen Roberts Intl., returning Thu, Mar 25, priced at $397 just found
Fri, Sep 18 - Thu, Sep 24
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$401 Roundtrip, found 3 days ago
$401
Roundtrip
found 3 days ago
Select Air Canada flight, departing Fri, Sep 18 from O'Hare Intl. to Owen Roberts Intl., returning Thu, Sep 24, priced at $401 found 3 days ago
Sun, Sep 20 - Thu, Sep 24
LGA
LaGuardia
GCM
Owen Roberts Intl.
$401 Roundtrip, found 6 days ago
$401
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sun, Sep 20 from LaGuardia to Owen Roberts Intl., returning Thu, Sep 24, priced at $401 found 6 days ago
OriginDestinationTravel DatesFlights From*
YYZGeorge TownSeptember 7 to September 14$326
JFKGeorge TownSeptember 7 to September 13$331
BOSGeorge TownAugust 23 to September 13$363
YULGeorge TownOctober 25 to November 1$369
ORDGeorge TownSeptember 9 to September 14$401
JFKLittle CaymanSeptember 7 to September 13$437
JFKWest EndOctober 5 to October 11$467
LHRGeorge TownOctober 21 to October 30$846
YYZWest EndAugust 19 to August 26$983
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
BOSGeorge TownAugust 1 to August 8$570
YYZGeorge TownAugust 1 to August 8$844
JFKGeorge TownAugust 1 to August 4$891
ORDGeorge TownAugust 1 to August 8$1,483
LHRGeorge TownAugust 2 to August 3$3,535
*Prices include taxes and fees

Best Cayman Islands Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Grand Cayman by IHG
4.5-star property

Hotel Indigo Grand Cayman by IHG

Oct 21 - Oct 25

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 $1,331, price is now $909 per person
$909
per person
found 1 day ago
Black Urchin
4.5-star property

Black Urchin

Oct 21 - Oct 25

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 $6,562, price is now $3,926 per person
$3,926
per person
found 1 day ago
The Reef Beach Resort, East End, Grand Cayman
3.5-star property

The Reef Beach Resort, East End, Grand Cayman

Aug 2 - Aug 8

6 night stay

Boston (BOS) to George Town (GCM)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,930, price is now $1,159 per person
$1,159
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 🏨

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.
9.8/10 Exceptional! (771 reviews)
"So great for our family of four. The beach staff was stand out amazing."

Reviewed on Jul 24, 2026

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.
9.6/10 Exceptional! (1,001 reviews)
"Wonderful vacation with kids. So convenient to walk right out on the beach with toys and activities. Food was great. Staff was amazing. My only wish is that the towels & cups were more “Ritz”. Basic plastic cups, basic tan towels etc. Make sure to stay in Ocean Tower if you’re planning on being near ..."

Reviewed on Jul 24, 2026

Opens in a new windowThe Ritz-Carlton, Grand Cayman
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! (1,002 reviews)
"Amazing staff- everytime"

Reviewed on Jul 24, 2026

Opens in a new windowThe Locale Hotel Grand Cayman
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
389 West Bay Road Seven Mile Beach Grand Cayman
Book a stay at this 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 Governor's Beach are located nearby.
Opens in a new windowGrand 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 $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 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. $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 $3,535. 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.

Explore More Ways to Travel with Travelocity