Cheap Flights to Cayman Islands from $62 (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

panoramic landscape aerial view of the tropical paradise of the cayman islands in the caribbean sea

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.

Sun, Mar 22 - Thu, Mar 26
FLL
Fort Lauderdale - Hollywood Intl.
GCM
Owen Roberts Intl.
$223 Roundtrip, found 5 hours ago
$223
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Sun, Mar 22 from Fort Lauderdale - Hollywood Intl. to Owen Roberts Intl., returning Thu, Mar 26, priced at $223 found 5 hours ago
Sat, Mar 28 - Tue, Mar 31
FLL
Fort Lauderdale - Hollywood Intl.
GCM
Owen Roberts Intl.
$270 Roundtrip, found 2 days ago
$270
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Mar 28 from Fort Lauderdale - Hollywood Intl. to Owen Roberts Intl., returning Tue, Mar 31, priced at $270 found 2 days ago
Thu, Apr 30 - Mon, May 4
MIA
Miami Intl.
GCM
Owen Roberts Intl.
$287 Roundtrip, found 1 day ago
$287
Roundtrip
found 1 day ago
Select Cayman Airways flight, departing Thu, Apr 30 from Miami Intl. to Owen Roberts Intl., returning Mon, May 4, priced at $287 found 1 day ago
Fri, Nov 6 - Wed, Nov 11
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$288 Roundtrip, found 6 days ago
$288
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Nov 6 from Logan Intl. to Owen Roberts Intl., returning Wed, Nov 11, priced at $288 found 6 days ago
Sat, Mar 21 - Sat, Mar 28
TPA
Tampa Intl.
GCM
Owen Roberts Intl.
$293 Roundtrip, found 2 days ago
$293
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Mar 21 from Tampa Intl. to Owen Roberts Intl., returning Sat, Mar 28, priced at $293 found 2 days ago
Fri, May 15 - Sat, May 23
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$303 Roundtrip, found 5 days ago
$303
Roundtrip
found 5 days ago
Select United flight, departing Fri, May 15 from Logan Intl. to Owen Roberts Intl., returning Sat, May 23, priced at $303 found 5 days ago
Mon, Sep 14 - Sun, Sep 20
JFK
John F. Kennedy Intl.
GCM
Owen Roberts Intl.
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
Select Cayman Airways flight, departing Mon, Sep 14 from John F. Kennedy Intl. to Owen Roberts Intl., returning Sun, Sep 20, priced at $314 found 1 day ago
Sun, Jun 14 - Tue, Jun 16
LGA
LaGuardia
GCM
Owen Roberts Intl.
$325 Roundtrip, found 3 days ago
$325
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Jun 14 from LaGuardia to Owen Roberts Intl., returning Tue, Jun 16, priced at $325 found 3 days ago
OriginDestinationTravel DatesFlights From*
YYZGeorge TownApril 9 to April 16$292
BOSGeorge TownMay 15 to May 23$303
LGAGeorge TownJune 14 to June 16$325
ORDGeorge TownApril 2 to April 9$347
YULGeorge TownApril 11 to April 17$354
JFKWest EndMay 10 to May 15$531
LHRGeorge TownApril 14 to April 21$1,012
FCOGeorge TownApril 1 to April 7$1,097
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
YYZGeorge TownMarch 20 to March 26$374
LGAGeorge TownMarch 22 to March 28$389
BOSGeorge TownMarch 21 to March 28$482
ORDGeorge TownMarch 22 to March 28$610
*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

Apr 29 - May 4

5 night stay

Chicago (CHI) to George Town (GCM)

American Airlines • Non-stop roundtrip • Coach
Price was $1,779, price is now $1,186 per person
$1,186
per person
found 1 day ago
Ocean Paradise
4.0-star property

Ocean Paradise

Jun 6 - Jun 10

4 night stay

Chicago (CHI) to George Town (GCM)

American Airlines • Coach

George Town (GCM) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $2,772, price is now $1,936 per person
$1,936
per person
found 1 day ago
The Westin Grand Cayman Seven Mile Beach Resort & Spa
4.5-star property

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Apr 9 - Apr 15

6 night stay

Chicago (CHI) to George Town (GCM)

Spirit Airlines • Non-stop • Coach

George Town (GCM) to Chicago (CHI)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $4,116, price is now $2,902 per person
$2,902
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Chicago 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 Port of Georgetown are located nearby.
9.8/10 Exceptional! (552 reviews)
By 7 am all the pool chairs were spoken for even though by 11 am more than half still never had people sitting in them (some going to beach!) Disappointing that staff never dealt with that. Food - the menus were a weird mixture. It would have been nice to have some salads and local food - jerk chicken, ...

Reviewed on Mar 16, 2026

Opens in a new windowHotel Indigo Grand Cayman by IHG
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 Seven Mile Beach are located nearby.
8.8/10 Excellent! (1,005 reviews)
AC did not cool below 73

Reviewed on Mar 15, 2026

Opens in a new windowGrand Cayman Marriott Resort
The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

4.5 out of 5
Seven Mile Beach Seven Mile Beach Grand Cayman
Book a stay at this luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa, and 6 restaurants. 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.
9.2/10 Wonderful! (1,007 reviews)
Did not need parking, staff was nice I didn’t really hang in the swim up bar once I found out we had to pay for everything that’s not fun I see cheaper resorts that would have done the same thing for a 3 of the price I paid I did not eat at the restaurants on the resort it’s many thing to chose from ...

Reviewed on Mar 15, 2026

Opens in a new windowThe Westin Grand Cayman Seven Mile Beach Resort & Spa
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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 Seven Mile Beach and Port of Georgetown are located nearby.
9.6/10 Exceptional! (1,006 reviews)
Beautiful beach and hotel. Great food and service!

Reviewed on Mar 15, 2026

Opens in a new windowThe Ritz-Carlton, 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 $223. 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 March 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. $223 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 $223 and $1,097. 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