$71 Cheap flights to Cayman Islands
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
Top places to visit in Cayman Islands
Cheap flights to Cayman Islands from $71 One Way, $237 Round Trip
$237 return flights and $71 one-way flights to Cayman Islands were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
Chicago
GCM
Grand Cayman
$237 Roundtrip, found 11 hours ago
$237
Roundtrip
found 11 hours ago
EWR
New York
GCM
Grand Cayman
$246 Roundtrip, found 4 days ago
$246
Roundtrip
found 4 days ago
MIA
Miami
GCM
Grand Cayman
$246 Roundtrip, just found
$246
Roundtrip
just found
JFK
New York
GCM
Grand Cayman
$246 Roundtrip, found 6 days ago
$246
Roundtrip
found 6 days ago
LGA
New York
GCM
Grand Cayman
$260 Roundtrip, found 5 days ago
$260
Roundtrip
found 5 days ago
BOS
Boston
GCM
Grand Cayman
$265 Roundtrip, found 9 hours ago
$265
Roundtrip
found 9 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LGA | George Town | December 26 to December 31 | $524 |
| BOS | George Town | December 26 to January 13 | $647 |
| YYZ | George Town | December 28 to December 31 | $683 |
| JFK | Little Cayman | December 28 to January 6 | $847 |
| ORD | George Town | December 28 to January 2 | $988 |
| YUL | George Town | December 26 to December 28 | $1,030 |
Find The Perfect Hotel For After Your Flight
Score Epic Cayman Islands Accommodation Deals
Sunshine Suites Resort
1465 Esterley Tibbetts Seven Mile Beach Grand Cayman
$463 nightly
The price is $517 total per night from Jan 4 to Jan 5
$517 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Book a stay at this beach hotel in Seven Mile Beach. Enjoy breakfast (surcharge), room service, and beach cabanas (surcharge). Our guests praise the restaurant ...
8.8/10 Excellent! (1,000 reviews)
Newly renovated. Clean rooms. Pool and restaurant wasn’t open but we had full access to the Westin facilities where we spent the day, which was great!
Reviewed on Dec 8, 2025
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way Seven Mile Beach Grand Cayman
$899 nightly
The price is $1,005 total per night from Jan 4 to Jan 5
$1,005 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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 ...
9.8/10 Exceptional! (970 reviews)
The hotel is beautiful, the food is delicious, and the staff are very friendly and welcoming!! The Sunday Brunch is a must! :) Would definitely stay there again :) Iesha
Reviewed on Dec 17, 2025
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Seven Mile Beach Seven Mile Beach Grand Cayman
$917 nightly
The price is $1,026 total per night from Jan 4 to Jan 5
$1,026 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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 ...
9/10 Wonderful! (1,001 reviews)
Our room was good - nice space and very clean. Friendly staff. The location on Seven Mile Beach is great. The $75 per day resort fee seems excessive, especially since we did not use the Fitness Center, Yoga Classes, etc. A word of advice - skip the Tortuga Grill special food nights. We found the ...
Reviewed on Dec 20, 2025
Save an average of 15% on thousands of hotels when you're signed in
Grand Cayman Marriott Resort
389 West Bay Road Seven Mile Beach Grand Cayman
$751 nightly
The price is $839 total per night from Jan 4 to Jan 5
$839 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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 ...
8.8/10 Excellent! (1,002 reviews)
Had very pleasant stay for a short 4 days getaway to 7MB. Staff overall extremely friendly and welcoming. We asked for an extra robe and slippers, they were brought up right away. No complaints.
Reviewed on Dec 17, 2025
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.
Our Top Cayman Islands Apartment Hotels
Sunshine Suites Resort
1465 Esterley Tibbetts Seven Mile Beach Grand Cayman
$463 nightly
The price is $517 total per night from Jan 4 to Jan 5
$517 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Book a stay at this beach hotel in Seven Mile Beach. Enjoy breakfast (surcharge), room service, and beach cabanas (surcharge). Our guests praise the restaurant ...
8.8/10 Excellent! (1,000 reviews)
Newly renovated. Clean rooms. Pool and restaurant wasn’t open but we had full access to the Westin facilities where we spent the day, which was great!
Reviewed on Dec 8, 2025
Holiday Inn Resort Grand Cayman by IHG
278 Crighton Drive West Bay Grand Cayman
Fully refundable
$411 nightly
The price is $454 total per night from Dec 24 to Dec 25
$454 total
Dec 24 - Dec 25
Total with taxes and fees
Book a stay at this beach hotel in West Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.2/10 Very Good! (655 reviews)
Friendly staff. Everything I needed was there.
Reviewed on Dec 15, 2025
Wyndham Reef Resort Grand Cayman
2221 Queens Highway East End Grand Cayman
Book a stay at this beach resort in East End. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (1,021 reviews)
The resort is located on the east side of the island. The advantage here is that it's quiet with all a lot of traffic. Disadvantage is that there are only with you restaurants and other off-resort activities. My personal recommendadition is to rent a car If you plan on checking out the entire island. ...
Reviewed on Dec 21, 2025
Save an average of 15% on thousands of hotels when you're signed in
Seven Mile Beach Resort & Club
19 D Piper Way, West Bay Road Seven Mile Beach Grand Cayman
$413 nightly
The price is $461 total per night from Jan 4 to Jan 5
$461 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Book a stay at this beach hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a free beach shuttle. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (375 reviews)
The room was very large and the kitchen had all the amenities needed for cooking and groceries. Loved the screened in balcony and the pool. The staff, especially Grace, was amazing! We appreciated the daily shuttles to the beach and the activities they offered at the resort. The location was perfect! ...
Reviewed on Dec 19, 2025
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.
Score Epic Cayman Islands Accommodation Deals
Hampton by Hilton Grand Cayman Seven Mile Beach
22 Piper Way Seven Mile Beach
Fully refundableReserve now, pay when you stay
$424 nightly
The price is $474 total per night from Dec 24 to Dec 25
$474 total
Dec 24 - Dec 25
Total with taxes and fees
Stay at this resort in Seven Mile Beach. Enjoy free breakfast, free parking, and a beach locale. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (659 reviews)
Morning staff in general was very kind and allowed me to check out 1 hour late
Reviewed on Dec 20, 2025
Grand Cayman Marriott Resort
389 West Bay Road Seven Mile Beach Grand Cayman
$751 nightly
The price is $839 total per night from Jan 4 to Jan 5
$839 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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 ...
8.8/10 Excellent! (1,002 reviews)
Had very pleasant stay for a short 4 days getaway to 7MB. Staff overall extremely friendly and welcoming. We asked for an extra robe and slippers, they were brought up right away. No complaints.
Reviewed on Dec 17, 2025
Hotel Indigo Grand Cayman by IHG
32 Seafire Way Seven Mile Beach West Bay
$604 nightly
The price is $675 total per night from Jan 12 to Jan 13
$675 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
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 ...
9.6/10 Exceptional! (446 reviews)
Spectacular
Reviewed on Dec 21, 2025
Save an average of 15% on thousands of hotels when you're signed in
The Ritz-Carlton, Grand Cayman
West Bay Road Seven Mile Beach Grand Cayman
$1,119 nightly
The price is $1,253 total per night from Jan 12 to Jan 13
$1,253 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
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. ...
9.4/10 Exceptional! (1,001 reviews)
Best location, beach is the best in the Carribean. Service, food and resort was well acquainted.
Reviewed on Dec 18, 2025
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.
Family Friendly Hotels in Cayman Islands
Grand Cayman Marriott Resort
389 West Bay Road Seven Mile Beach Grand Cayman
$751 nightly
The price is $839 total per night from Jan 4 to Jan 5
$839 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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 ...
8.8/10 Excellent! (1,002 reviews)
Families like: Outdoor pool, kids club, babysitting, close to beach
Travelers say...
Had very pleasant stay for a short 4 days getaway to 7MB. Staff overall extremely friendly and welcoming. We asked for an extra robe and slippers, they were brought up right away. No complaints.
Reviewed on Dec 17, 2025
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way Seven Mile Beach Grand Cayman
$899 nightly
The price is $1,005 total per night from Jan 4 to Jan 5
$1,005 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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 ...
9.8/10 Exceptional! (970 reviews)
The hotel is beautiful, the food is delicious, and the staff are very friendly and welcoming!! The Sunday Brunch is a must! :) Would definitely stay there again :) Iesha
Reviewed on Dec 17, 2025
Aqua Bay Club Condos
W Bay Rd Seven Mile Beach Grand Cayman
Book a stay at this beach condo in Seven Mile Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Seven Mile Beach and Port of Georgetown ...
9.6/10 Exceptional! (88 reviews)
Quiet little resort with amazing beach. Snorkeling right off the beach. Everything was perfect. Staff was very nice. Will visit again.
Reviewed on Nov 13, 2025
Save an average of 15% on thousands of hotels when you're signed in
Wyndham Reef Resort Grand Cayman
2221 Queens Highway East End Grand Cayman
Book a stay at this beach resort in East End. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (1,021 reviews)
The resort is located on the east side of the island. The advantage here is that it's quiet with all a lot of traffic. Disadvantage is that there are only with you restaurants and other off-resort activities. My personal recommendadition is to rent a car If you plan on checking out the entire island. ...
Reviewed on Dec 21, 2025
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.
Need a Car For After Your Flight?
Economy
Chevrolet Spark or similar
Compact
Ford Focus or similar
Midsize
Toyota Corolla or similar
SUV
Jeep Compass or similar
Cayman Islands
Save money on your flights to Cayman Islands as well as on hotel and car packages.
Free Fees
Snap up cheap Cayman Islands flights at Orbitz, and pay no booking fees. We also don’t charge fees when your plans change or are cancelled. While you’re there, check out our low fare deals on flights to other locations besides flights to Cayman Islands.
Everyday Is a Great Day to Save Even More
Get bonus points from Orbitz, the best discount travel planner in the business. Use your Orbitz Visa to take advantage of sales on Cayman Islands flights, or pile on points by using it for gas, groceries, and other everyday goods and services. Pack your wallet with even more savings using our cutting-edge suite of mobile tools.
Mix and Match
At Orbitz, we turned a great idea from the world of fashion into another way for you to save money. When you shop our low cost tickets on flights to any destination, don’t be afraid to mix and match different airlines for maximum savings on your Cayman Islands flights air ticket. Save more on air travel every day in every way at Orbitz.
Frequently asked questions
More to Explore
- 5 Star Hotels in Grand Cayman
- B&B in Grand Cayman
- Condo Rentals in Grand Cayman
- Cottages in Grand Cayman
- All Inclusive Resorts & in Grand Cayman
- Beach Resorts & in Grand Cayman
- Boutique Hotels in Grand Cayman
- Kid Friendly Hotels in Grand Cayman
- Golf Resorts & in Grand Cayman
- Grand Cayman Hotels
- Vacation Homes in Grand Cayman
- Villas in Grand Cayman
- Flights to Grand Cayman
- Flights from Key West to Grand Cayman
- Flights from Wilmington to Grand Cayman
- Flights from Atlanta to Grand Cayman
- Flights from Austin to Grand Cayman
- Flights from Baltimore to Grand Cayman
- Flights from Boston to Grand Cayman
- Flights from Charlotte to Grand Cayman
- Flights from Chicago to Grand Cayman
- Flights from Cincinnati to Grand Cayman
- Flights from Cleveland to Grand Cayman
- Flights from Columbus to Grand Cayman
- Flights from Dallas to Grand Cayman
- Flights from Denver to Grand Cayman
- Flights from Detroit to Grand Cayman
- Flights from Houston to Grand Cayman
- Flights from Indianapolis to Grand Cayman
- Flights from Kansas City to Grand Cayman
- Flights from Las Vegas to Grand Cayman
- Flights from Los Angeles to Grand Cayman
- Flights from Manila to Grand Cayman
- Flights from Memphis to Grand Cayman
- Flights from Mexico City to Grand Cayman
- Flights from Miami to Grand Cayman
- Flights from Minneapolis - St. Paul to Grand Cayman
- Flights from Nashville to Grand Cayman
- Flights from New Orleans to Grand Cayman
- Flights from New York to Grand Cayman
- Flights from Orlando to Grand Cayman
- Flights from Ottawa to Grand Cayman
- Flights from Philadelphia to Grand Cayman
- Flights from Phoenix to Grand Cayman
- Flights from Portland to Grand Cayman
- Flights from Salt Lake City to Grand Cayman
- Flights from San Antonio to Grand Cayman
- Flights from San Francisco to Grand Cayman
- Flights from Seattle to Grand Cayman
- Flights from St. Louis to Grand Cayman
- Flights from Vancouver to Grand Cayman
- Flights from Washington to Grand Cayman
- Flights from Cancun to Grand Cayman
- Flights from Charleston to Grand Cayman
- Flights from Hartford to Grand Cayman
- Flights from Providence to Grand Cayman
- Flights from Kingston to Grand Cayman
- Flights from Sacramento to Grand Cayman
- Flights from Montego Bay to Grand Cayman
- Flights from Portland to Grand Cayman
- Flights from Omaha to Grand Cayman
- Flights from Port of Spain to Grand Cayman
- Flights from San Juan to Grand Cayman
- Flights from Myrtle Beach to Grand Cayman
- Flights from Des Moines to Grand Cayman
- Flights from Pittsburgh to Grand Cayman
- Flights from Fort Lauderdale to Grand Cayman
- Flights from Newark to Grand Cayman
- Flights from Richmond to Grand Cayman
- Flights from Syracuse to Grand Cayman
- Flights from Nassau to Grand Cayman
- Flights from Tulsa to Grand Cayman
- Flights from Daytona Beach to Grand Cayman
- Flights from Bentonville - Fayetteville to Grand Cayman
- Flights from Milwaukee to Grand Cayman
- Flights from Buffalo to Grand Cayman
- Flights from Sarasota to Grand Cayman
- Flights from Fort Myers to Grand Cayman
- Flights from Little Rock to Grand Cayman
- Flights from Shreveport to Grand Cayman
- Flights from Grand Cayman
- Flights from Norfolk - Virginia Beach to Grand Cayman
- Flights from Springfield to Grand Cayman
- Flights from Rochester to Grand Cayman
- Flights from Oklahoma City to Grand Cayman
- Flights from Knoxville to Grand Cayman
- Flights from Birmingham to Grand Cayman
- Flights from Tampa to Grand Cayman
- Flights from Jacksonville to Grand Cayman
- Flights from Peoria to Grand Cayman
- Flights from Louisville to Grand Cayman
- Flights from Grand Rapids to Grand Cayman
- Flights from Albany to Grand Cayman
- Flights from Savannah to Grand Cayman
- Flights from Greenville - Spartanburg to Grand Cayman
- Flights from Fargo to Grand Cayman
- Flights from Sioux Falls to Grand Cayman
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.
