$105 Cheap flights to Cayman Islands
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Cheap flights to Cayman Islands from $105 One Way, $151 Round Trip
$151 return flights and $105 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.
GCM
Grand Cayman
CYB
Cayman Brac
$151 Roundtrip, found 3 days ago
$151
Roundtrip
found 3 days ago
GCM
Grand Cayman
LYB
Little Cayman
$169 Roundtrip, found 3 days ago
$169
Roundtrip
found 3 days ago
MIA
Miami
GCM
Grand Cayman
$325 Roundtrip, just found
$325
Roundtrip
just found
MIA
Miami
GCM
Grand Cayman
$325 Roundtrip, found 2 hours ago
$325
Roundtrip
found 2 hours ago
MIA
Miami
CYB
Cayman Brac
$348 Roundtrip, found 1 day ago
$348
Roundtrip
found 1 day ago
EWR
New York
GCM
Grand Cayman
$360 Roundtrip, found 3 days ago
$360
Roundtrip
found 3 days ago
JFK
New York
GCM
Grand Cayman
$365 Roundtrip, just found
$365
Roundtrip
just found
BOS
Boston
GCM
Grand Cayman
$371 Roundtrip, found 3 hours ago
$371
Roundtrip
found 3 hours ago
LGA
New York
GCM
Grand Cayman
$371 Roundtrip, found 10 hours ago
$371
Roundtrip
found 10 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| YYZ | George Town | June 21 to June 28 | $448 |
| EWR | George Town | June 20 to June 24 | $503 |
| BOS | George Town | June 21 to June 24 | $589 |
| ORD | George Town | June 22 to June 29 | $688 |
| LHR | George Town | June 20 to July 18 | $2,023 |
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
Fully refundableReserve now, pay when you stay
Stay at this 4-star beach hotel in Seven Mile Beach. Enjoy breakfast (surcharge), room service, and beach cabanas (surcharge). Our guests praise the restaurant ...
8.8/10 Excellent! (1,001 reviews)
"We had a wonderful stay at Sunshine Suites. The new renovated rooms were nicely done and everything was updated and clean. I can’t wait to see what it will look like when the rest of the renovations are complete (other buildings, the pool and the grill were closed for renovations during our stay). ..."
Reviewed on Jun 15, 2025
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way, Seven Mile Beach, Grand Cayman
Stay at this 5-star 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! (821 reviews)
"Staff was kind as always , rooms and hotel so clean, thank you so much"
Reviewed on Jun 1, 2025
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Seven Mile Beach, P.O. Box 30620, Seven Mile Beach, Grand Cayman
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy a full-service spa, 6 restaurants, and a private beach. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,001 reviews)
"Because I booked the trip through Expedia, I did not get benefits that I would have received (and was entitled to) like free breakfasts. To get those, I was advised that I had to book directly with Marriott."
Reviewed on Jun 15, 2025
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Grand Cayman Marriott Resort
389 West Bay Road, Po Box 30371, Seven Mile Beach, Grand Cayman
Stay at this 4.5-star 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! (1,000 reviews)
"The staff went above and beyond to my our stay perfect."
Reviewed on Jun 9, 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
Fully refundableReserve now, pay when you stay
Stay at this 4-star beach hotel in Seven Mile Beach. Enjoy breakfast (surcharge), room service, and beach cabanas (surcharge). Our guests praise the restaurant ...
8.8/10 Excellent! (1,001 reviews)
"We had a wonderful stay at Sunshine Suites. The new renovated rooms were nicely done and everything was updated and clean. I can’t wait to see what it will look like when the rest of the renovations are complete (other buildings, the pool and the grill were closed for renovations during our stay). ..."
Reviewed on Jun 15, 2025
Holiday Inn Resort Grand Cayman by IHG
278 Crighton Drive, West Bay, Grand Cayman
Fully refundable
Stay at this 3.5-star beach hotel in West Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (620 reviews)
"I like the services of the staff and enjoy the food and drinks offerings at the restaurant. The deck to view the sunrise is a nice addition."
Reviewed on May 30, 2025
Wyndham Reef Resort Grand Cayman
2221 Queens Highway, Collier's Bay, East End, Grand Cayman
Stay at this 3.5-star 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. ...
8.2/10 Very Good! (1,000 reviews)
"This bed was the most comfortable, but I’ve slept in in a long time. I love Wyndham, the restaurant was just a quick walk. The store and liquor store are right across the street within walking distance."
Reviewed on Jun 4, 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
Stay at this 3-star beach hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (344 reviews)
"Property was very nice! Great location. Short and easy walkway to the beach and shops and restaurants. Quiet and beautiful area. Room was perfect, 2 bedroom and 2 baths with full kitchen and laundry area. Will definitely stay here again."
Reviewed on May 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.
Score Epic Cayman Islands Accommodation Deals
The Ritz-Carlton, Grand Cayman
West Bay Road, PO Box 32348 KY1-1209, Seven Mile Beach, Grand Cayman
Stay at this 5-star luxury resort in Seven Mile Beach. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff in our ...
9.4/10 Exceptional! (990 reviews)
"Upgraded to the hotel lounge, it is a must, from housekeeping to lounge, everybody were great!"
Reviewed on Jun 11, 2025
Hampton by Hilton Grand Cayman Seven Mile Beach
22 Piper Way, Seven Mile Beach
Fully refundableReserve now, pay when you stay
Stay at this 4-star 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. ...
9/10 Wonderful! (549 reviews)
"Comfortable"
Reviewed on Jun 15, 2025
Hotel Indigo Grand Cayman by IHG
32 Seafire Way, Seven Mile Beach, West Bay
Fully refundable
Stay at this 4.5-star luxury hotel in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 4 restaurants. Popular attractions Seven Mile Beach and Port ...
9.6/10 Exceptional! (273 reviews)
"Very nice and new property. Staff all very accommodating and helpful. Rooms not huge but god for our purposes… we weren’t there to stay indoors anyhow ! Dining options fairly pricy so we ate elsewhere. Pool very well done. Easy access to Seven Mile Beach, easy 5 minute leisurely stroll. Valet staff ..."
Reviewed on Jun 10, 2025
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
Stay at this 3.5-star beach hotel in Seven Mile Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (895 reviews)
"Nice rooms, friendly and professional staff. Location is great."
Reviewed on Jun 15, 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, Po Box 30371, Seven Mile Beach, Grand Cayman
Stay at this 4.5-star 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! (1,000 reviews)
Families like: Outdoor pool, kids club, babysitting, close to beach
Travelers say...
"The staff went above and beyond to my our stay perfect."
Reviewed on Jun 9, 2025
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way, Seven Mile Beach, Grand Cayman
Stay at this 5-star 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! (821 reviews)
"Staff was kind as always , rooms and hotel so clean, thank you so much"
Reviewed on Jun 1, 2025
Aqua Bay Club Condos
W Bay Rd, P.O. Box 30091, Seven Mile Beach, Grand Cayman
Stay at this 3-star 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! (85 reviews)
"We loved being at this end of seven mile beach, nice and quiet property. Loved having a screened in patio."
Reviewed on Apr 25, 2025
Save an average of 15% on thousands of hotels when you're signed in
Wyndham Reef Resort Grand Cayman
2221 Queens Highway, Collier's Bay, East End, Grand Cayman
Stay at this 3.5-star 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. ...
8.2/10 Very Good! (1,000 reviews)
"This bed was the most comfortable, but I’ve slept in in a long time. I love Wyndham, the restaurant was just a quick walk. The store and liquor store are right across the street within walking distance."
Reviewed on Jun 4, 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
More to explore for Cayman Islands
Cayman Islands
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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.