$100 Cheap flights to Cayman Islands
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Top places to visit in Cayman Islands
Cheap flights to Cayman Islands from $100 One Way, $287 Round Trip
$287 return flights and $100 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.
MIA
Miami
GCM
Grand Cayman
$287 Roundtrip, just found
$287
Roundtrip
just found
MIA
Miami
GCM
Grand Cayman
$292 Roundtrip, just found
$292
Roundtrip
just found
JFK
New York
GCM
Grand Cayman
$319 Roundtrip, found 8 hours ago
$319
Roundtrip
found 8 hours ago
EWR
New York
GCM
Grand Cayman
$319 Roundtrip, found 21 hours ago
$319
Roundtrip
found 21 hours ago
LGA
New York
GCM
Grand Cayman
$333 Roundtrip, found 6 hours ago
$333
Roundtrip
found 6 hours ago
MIA
Miami
CYB
Cayman Brac
$356 Roundtrip, found 4 days ago
$356
Roundtrip
found 4 days ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| BOS | George Town | June 20 to June 27 | $331 |
| LGA | George Town | June 19 to June 24 | $365 |
| YUL | George Town | June 20 to June 25 | $555 |
| YYZ | George Town | June 21 to June 26 | $675 |
| ORD | George Town | June 20 to June 27 | $892 |
| LHR | George Town | June 19 to July 3 | $1,455 |
Find The Perfect Hotel For After Your Flight
Score Epic Cayman Islands Accommodation Deals
The Sunshine Hotel and Suites
1465 Esterley Tibbetts Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$270 nightly
The price is $302 total per night from Jun 16 to Jun 17
$302 total
Jun 16 - Jun 17
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 ...
9/10 Wonderful! (1,006 reviews)
"The staff always greeted you with a smile. I loved How special they made my mom feel for her birthday. Simple and meaningful ways to just be overall good and nice people. Amenities at Westin was a huge plus also. Hotel is right were you need to be on 7mile. Highly recommend!"
Reviewed on Jun 9, 2026
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way Seven Mile Beach Grand Cayman
Fully refundable
$945 nightly
The price is $1,056 total per night from Jul 15 to Jul 16
$1,056 total
Jul 15 - Jul 16
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! (1,002 reviews)
"Kimpton Seafire did not disappoint. It’s been 5+ years since our last visit and I was thrilled to see the quality (facilities, staff, cleanliness, etc) maintained the same high standard."
Reviewed on Jun 5, 2026
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Seven Mile Beach Seven Mile Beach Grand Cayman
$804 nightly
The price is $909 total per night from Jul 5 to Jul 6
$909 total
Jul 5 - Jul 6
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 ...
9.2/10 Wonderful! (1,002 reviews)
"I’m comparing it to the Palm Heights and the Ritz Carlton, so it may not be fair. It was a louder place with loud people. Bands playing in the lobby at night. Bar filled with people. Lots of families. Not my usual stay so I wasn’t impressed."
Reviewed on Jun 12, 2026
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
Fully refundableReserve now, pay when you stay
$384 nightly
The price is $436 total per night from Jul 14 to Jul 15
$436 total
Jul 14 - Jul 15
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 ...
9/10 Wonderful! (1,009 reviews)
"They are building a wall to prevent beach erosion so the beach outside the hotel is inaccessible and you have to walk quite a distance to get beach stuff"
Reviewed on Jun 11, 2026
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
The Sunshine Hotel and Suites
1465 Esterley Tibbetts Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$270 nightly
The price is $302 total per night from Jun 16 to Jun 17
$302 total
Jun 16 - Jun 17
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 ...
9/10 Wonderful! (1,006 reviews)
"The staff always greeted you with a smile. I loved How special they made my mom feel for her birthday. Simple and meaningful ways to just be overall good and nice people. Amenities at Westin was a huge plus also. Hotel is right were you need to be on 7mile. Highly recommend!"
Reviewed on Jun 9, 2026
Holiday Inn Resort Grand Cayman by IHG
278 Crighton Drive West Bay Grand Cayman
Fully refundable
$229 nightly
The price is $253 total per night from Jul 15 to Jul 16
$253 total
Jul 15 - Jul 16
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! (677 reviews)
"The resort is nice for the value. We had to have our room changed twice because the first room smelled horrible and the second room didn't give us the view the first room gave us. The third room was miserable!!! We got the nice view.. but the ac didn't work. My husband has a medical condition that ..."
Reviewed on Jun 12, 2026
The Reef Beach Resort, East End, Grand Cayman
2221 Queens Highway East End Grand Cayman
Book a stay at this beach aparthotel in East End. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (1,075 reviews)
"Property was rebranded before we arrived and yes we knew of change but this would have been 2nd stay was good enough that we decided to come back with our daughter for her graduation present unfortunately it was nowhere near what we expected and our daughter was also disappointed. So we where left ..."
Reviewed on Jun 7, 2026
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
$255 nightly
The price is $288 total per night from Jul 6 to Jul 7
$288 total
Jul 6 - Jul 7
Total with taxes and fees
Book a stay at this beach hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (441 reviews)
"The room came stocked with everything you need, including a full kitchen and washer and dryer. The pool area was large, clean, and there were plenty of lounge chairs available during our stay. The closeness to the beach was great, just a very short walk. We would definitely stay there again."
Reviewed on Jun 6, 2026
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
Hotel Indigo Grand Cayman by IHG
32 Seafire Way Seven Mile Beach West Bay
$289 nightly
The price is $324 total per night from Jul 15 to Jul 16
$324 total
Jul 15 - Jul 16
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 Governor's ...
9.8/10 Exceptional! (675 reviews)
"This place is outstanding. The staff go above and beyond to make your stay exceptional. Trust me, won’t regret staying there. The room was spacious and so clean. The bed was the most comfortable that I have slept in. It was so quiet and peaceful. The restaurant Catalina so worth it and the Pom-Pom ..."
Reviewed on Jun 14, 2026
Grand Cayman Marriott Resort
389 West Bay Road Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$384 nightly
The price is $436 total per night from Jul 14 to Jul 15
$436 total
Jul 14 - Jul 15
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 ...
9/10 Wonderful! (1,009 reviews)
"They are building a wall to prevent beach erosion so the beach outside the hotel is inaccessible and you have to walk quite a distance to get beach stuff"
Reviewed on Jun 11, 2026
The Ritz-Carlton, Grand Cayman
West Bay Road Seven Mile Beach Grand Cayman
$1,086 nightly
The price is $1,216 total per night from Jul 11 to Jul 12
$1,216 total
Jul 11 - Jul 12
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. ...
9.6/10 Exceptional! (1,003 reviews)
"Awesome place. We’ve been there several times. Family friendly but still great for us, an older couple. You won’t regret staying here. The entire staff is very friendly and accommodating. We’ll be back again."
Reviewed on May 31, 2026
Save an average of 15% on thousands of hotels when you're signed in
The Locale Hotel Grand Cayman
455 West Bay Road Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $216 total per night from Jun 17 to Jun 18
$216 total
Jun 17 - Jun 18
Total with taxes and fees
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 ...
9.4/10 Exceptional! (1,025 reviews)
"all good and really convenient for business meetings at Camama Bay"
Reviewed on Jun 14, 2026
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
Fully refundableReserve now, pay when you stay
$384 nightly
The price is $436 total per night from Jul 14 to Jul 15
$436 total
Jul 14 - Jul 15
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 ...
9/10 Wonderful! (1,009 reviews)
Families like: Outdoor pool, kids club, babysitting, close to beach
Travelers say...
"They are building a wall to prevent beach erosion so the beach outside the hotel is inaccessible and you have to walk quite a distance to get beach stuff"
Reviewed on Jun 11, 2026
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way Seven Mile Beach Grand Cayman
Fully refundable
$945 nightly
The price is $1,056 total per night from Jul 15 to Jul 16
$1,056 total
Jul 15 - Jul 16
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! (1,002 reviews)
"Kimpton Seafire did not disappoint. It’s been 5+ years since our last visit and I was thrilled to see the quality (facilities, staff, cleanliness, etc) maintained the same high standard."
Reviewed on Jun 5, 2026
Aqua Bay Club Condos
W Bay Rd Seven Mile Beach Grand Cayman
Book a stay at this beach aparthotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Seven Mile Beach and Governor's ...
Save an average of 15% on thousands of hotels when you're signed in
The Reef Beach Resort, East End, Grand Cayman
2221 Queens Highway East End Grand Cayman
Book a stay at this beach aparthotel in East End. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (1,075 reviews)
"Property was rebranded before we arrived and yes we knew of change but this would have been 2nd stay was good enough that we decided to come back with our daughter for her graduation present unfortunately it was nowhere near what we expected and our daughter was also disappointed. So we where left ..."
Reviewed on Jun 7, 2026
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.
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Cayman Islands
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Cheap Deals on Flights to Cayman Islands
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Miles or Points Toward Frequent Flyer Programs
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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.
