$91 Cheap flights to Cayman Islands

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Top places to visit in Cayman Islands

Cheap flights to Cayman Islands from $91 One Way, $287 Round Trip

$287 return flights and $91 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.

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
YYZGeorge TownSeptember 26 to September 29$324
BOSGeorge TownSeptember 27 to October 6$420
EWRGeorge TownSeptember 28 to November 30$506
LHRGeorge TownSeptember 26 to October 4$1,150
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Cayman Islands Accommodation Deals

Sunshine Suites Resort

Sunshine Suites Resort

4 out of 5
1465 Esterley Tibbetts, Seven Mile Beach, Grand Cayman
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! (1,000 reviews)
"Great place to be at!"

Reviewed on Aug 7, 2025

Opens in a new windowSunshine Suites Resort
Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way, Seven Mile Beach, Grand Cayman
Fully refundable
$589 nightly
The price is $659 total per night from Sep 26 to Sep 27
$659 total
Sep 26 - Sep 27
Total with taxes and fees
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! (900 reviews)
"Loved staying here will definitely return to this property the free wine bar at happy hour is great and love the library lounge they have just a cool vibe"

Reviewed on Sep 17, 2025

Opens in a new windowKimpton Seafire Resort + Spa by IHG
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, P.O. Box 30620, Seven Mile Beach, Grand Cayman
Fully refundableReserve now, pay when you stay
$543 nightly
The price is $607 total per night from Sep 26 to Sep 27
$607 total
Sep 26 - Sep 27
Total with taxes and fees
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 ...
9/10 Wonderful! (1,007 reviews)
"Hotel location superb Service excellent Nothing better"

Reviewed on Sep 18, 2025

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
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
389 West Bay Road, Po Box 30371, Seven Mile Beach, Grand Cayman
Fully refundableReserve now, pay when you stay
$415 nightly
The price is $464 total per night from Sep 24 to Sep 25
$464 total
Sep 24 - Sep 25
Total with taxes and fees
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! (1,006 reviews)
"The view from my room was ABSOLUTELY AMAZING! The staff was SUPERIOR! Ainah, at the front desk - I love you girl!!!! I will be visiting again! First Class!!!"

Reviewed on Sep 12, 2025

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.

Our Top Cayman Islands Apartment Hotels

Sunshine Suites Resort

Sunshine Suites Resort

4 out of 5
1465 Esterley Tibbetts, Seven Mile Beach, Grand Cayman
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! (1,000 reviews)
"Great place to be at!"

Reviewed on Aug 7, 2025

Opens in a new windowSunshine Suites Resort
Holiday Inn Resort Grand Cayman by IHG

Holiday Inn Resort Grand Cayman by IHG

3.5 out of 5
278 Crighton Drive, West Bay, Grand Cayman
Fully refundable
$190 nightly
The price is $210 total per night from Sep 27 to Sep 28
$210 total
Sep 27 - Sep 28
Total with taxes and fees
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! (637 reviews)
"Nice complex at a reasonable price, if a bit dated now."

Reviewed on Sep 17, 2025

Opens in a new windowHoliday Inn Resort Grand Cayman by IHG
Wyndham Reef Resort Grand Cayman

Wyndham Reef Resort Grand Cayman

3.5 out of 5
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! (1,010 reviews)
"It is very nice,food is very expensive and that is common on the Island. They are working on the Sargassum which Mother Nature controls that issue. It is a drive to most visited areas. The kitchen is nice to have,the studio could use a table to eat at. Ceiling fan needs to be set on a higher speed ..."

Reviewed on Aug 27, 2025

Opens in a new windowWyndham Reef Resort Grand Cayman
Save an average of 15% on thousands of hotels when you're signed in
Seven Mile Beach Resort & Club

Seven Mile Beach Resort & Club

3 out of 5
19 D Piper Way, West Bay Road, Seven Mile Beach, Grand Cayman
$254 nightly
The price is $284 total per night from Sep 24 to Sep 25
$284 total
Sep 24 - Sep 25
Total with taxes and fees
Stay at this 3-star 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! (360 reviews)
"Apartment was clean and comfortable. Pool was excellent!!!"

Reviewed on Sep 5, 2025

Opens in a new windowSeven Mile Beach Resort & Club
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

Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way, Seven Mile Beach, Grand Cayman
Fully refundable
$589 nightly
The price is $659 total per night from Sep 26 to Sep 27
$659 total
Sep 26 - Sep 27
Total with taxes and fees
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! (900 reviews)
"Loved staying here will definitely return to this property the free wine bar at happy hour is great and love the library lounge they have just a cool vibe"

Reviewed on Sep 17, 2025

Opens in a new windowKimpton Seafire Resort + Spa by IHG
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
West Bay Road, PO Box 32348 KY1-1209, Seven Mile Beach, Grand Cayman
Fully refundableReserve now, pay when you stay
$725 nightly
The price is $812 total per night from Oct 3 to Oct 4
$812 total
Oct 3 - Oct 4
Total with taxes and fees
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! (1,004 reviews)
"Shower tiny , no restroom close to the beach"

Reviewed on Sep 8, 2025

Opens in a new windowThe Ritz-Carlton, Grand Cayman
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
Fully refundable
$350 nightly
The price is $391 total per night from Sep 27 to Sep 28
$391 total
Sep 27 - Sep 28
Total with taxes and fees
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! (391 reviews)
"Location on the seven mile beach"

Reviewed on Sep 21, 2025

Opens in a new windowHotel Indigo Grand Cayman by IHG
Save an average of 15% on thousands of hotels when you're signed in
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
389 West Bay Road, Po Box 30371, Seven Mile Beach, Grand Cayman
Fully refundableReserve now, pay when you stay
$415 nightly
The price is $464 total per night from Sep 24 to Sep 25
$464 total
Sep 24 - Sep 25
Total with taxes and fees
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! (1,006 reviews)
"The view from my room was ABSOLUTELY AMAZING! The staff was SUPERIOR! Ainah, at the front desk - I love you girl!!!! I will be visiting again! First Class!!!"

Reviewed on Sep 12, 2025

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.

Family Friendly Hotels in Cayman Islands

Grand Cayman Marriott Resort
Great for families

Grand Cayman Marriott Resort

4.5 out of 5
389 West Bay Road, Po Box 30371, Seven Mile Beach, Grand Cayman
Fully refundableReserve now, pay when you stay
$415 nightly
The price is $464 total per night from Sep 24 to Sep 25
$464 total
Sep 24 - Sep 25
Total with taxes and fees
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! (1,006 reviews)

Families like: Outdoor pool, kids club, babysitting, close to beach

Travelers say...
"The view from my room was ABSOLUTELY AMAZING! The staff was SUPERIOR! Ainah, at the front desk - I love you girl!!!! I will be visiting again! First Class!!!"

Reviewed on Sep 12, 2025

Opens in a new windowGrand Cayman Marriott Resort
Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way, Seven Mile Beach, Grand Cayman
Fully refundable
$589 nightly
The price is $659 total per night from Sep 26 to Sep 27
$659 total
Sep 26 - Sep 27
Total with taxes and fees
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! (900 reviews)
"Loved staying here will definitely return to this property the free wine bar at happy hour is great and love the library lounge they have just a cool vibe"

Reviewed on Sep 17, 2025

Opens in a new windowKimpton Seafire Resort + Spa by IHG
Aqua Bay Club Condos

Aqua Bay Club Condos

3 out of 5
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! (87 reviews)
"Place is awesome, clean and a great stay. the beach out front has great snorkeling and is very clean. Will come back.."

Reviewed on Jul 20, 2025

Opens in a new windowAqua Bay Club Condos
Save an average of 15% on thousands of hotels when you're signed in
Wyndham Reef Resort Grand Cayman

Wyndham Reef Resort Grand Cayman

3.5 out of 5
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! (1,010 reviews)
"It is very nice,food is very expensive and that is common on the Island. They are working on the Sargassum which Mother Nature controls that issue. It is a drive to most visited areas. The kitchen is nice to have,the studio could use a table to eat at. Ceiling fan needs to be set on a higher speed ..."

Reviewed on Aug 27, 2025

Opens in a new windowWyndham Reef Resort 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.

Need a Car For After Your Flight?

Frequently asked questions

Which airlines fly to Cayman Islands?
Have a look at the deals from the 12 airlines that operate services to Cayman Islands. Whether you'd like to stretch out in the pointy end of the plane or save cash in economy, there'll be a seat for you. Head for Owen Roberts Intl. Airport (GCM) with one of these leading carriers:

  • American Airlines - 35 flights to Cayman Islands per month
  • Cayman Airways - 31 flights to Cayman Islands per month
  • Delta - 8 flights to Cayman Islands per month

How much is a flight to Cayman Islands?
Loads of excellent deals were had this week, with round-trip flights to Cayman Islands fluctuating between $287 and $1,150. But it was jet-setters arriving in from Tampa (TPA) who scored the top bargains. One-way tickets to Cayman Islands fell to just $91.
How to book the cheapest flight to Cayman Islands?
Snapping up cheap flights to Cayman Islands is as easy as booking your ticket with Orbitz. But if you'd love to make sure you're walking away with the best flight deals around, here are a few tips your budget will love:

  • Consider taking off from or landing at alternative airports to save money. Enter your preferred departure and arrival points in the form fields, then click on the 'Nearby airports' function below. It will list your options, if any.
  • If you're flexible with your travel plans, click on the 'Show flexible dates' option. It'll show the flight deals for the days around your selected departure. Fares often vary depending on what day of the week it is.
  • Hit 'Show options' to fine tune your search results. You can choose your preferred seating class and airline here. Under 'Sort & Filter' to the left, you can even specify whether you want to fly in the morning, afternoon or evening.
  • Once you've sorted out your travel dates, don't waste time booking your flight. Prices usually rise as the departure date gets closer.
  • Make even more savings on your adventure by bundling your flights, hotels and car rentals into one convenient package deal. Your budget will thank you.
  • If practical, don't fly during the busy season. Airfares significantly increase during school breaks, summer and around other vacation times like Easter and Thanksgiving.

What is the best time to book a flight to Cayman Islands?
Generally speaking, the cheapest time to book your airfare is January. This is followed by February and August. When seeking a cheap flight to Cayman Islands, it's always good to be ready to book. Cheap deals appear in an instant and don't hang around!
What day of the week is the cheapest to book a flight to Cayman Islands?
If you're after low-cost fares to Cayman Islands, the best days to book are Tuesdays, Wednesdays and Saturdays. With Orbitz (and some good timing!), an unbeatable flight deal will be all yours.
What is the cheapest day of the week to fly to Cayman Islands?
According to Orbitz data from 2020, you'll want to hop on a plane on a Monday to get cheap flights to Cayman Islands. Next most affordable day? Tuesday. Saturday will cost the most. So, think about departing early in the week if you want to book a wallet-friendly fare without paying premium prices.
What is the cheapest month to fly to Cayman Islands?
Get set to jet for less in August. This is generally the best month to get on a plane if you want cheap flights to Cayman Islands, Orbitz data shows. The costliest time to fly is June, so avoid this month if you can.
Which airlines allow free cancellation?
Things change, and we believe your flight should be able to as well. That's why Orbitz makes it a breeze to search for flights with no change fees and free cancellation. Just enter your travel details and then select "Filter by flexible change policies." Now that's peace of mind!
What do I need for the flight to Cayman Islands?
Whether you're accustomed to flying or it's your first time in the air, you can never be too prepared on your trip. Here are several things to keep in mind:

  • You'll need to take all applicable travel documents and your identification. How much depends on where you're departing from. At the time of booking, always use the exact name, gender and birth date as indicated on your government-issued ID.
  • A well-stocked carry-on bag is a must for any medium-haul flight. With a few hours or more to kill, you'll want something to keep you busy while in the air. We recommend a good book (or trashy magazine), and something to snack on.
  • Regardless what the season is, airplane cabins can get a little chilly. Carry an extra layer on board with you to stay nice and toasty.

How do I get cheap first-class/business deals to Cayman Islands?
If you think a first or business-class fare is beyond your reach, you may want to think again. Here are some terrific tips to help you pick up a premium flight to Cayman Islands for less:

  • Flexibility isn't just a yoga thing. Leave some room to move around your travel dates so you can pick up more affordable airfares when a huge sale drops.
  • Look for a low-cost carrier that offers business-class seats. They often come with extra legroom and a glass of Champagne — but at a more affordable price.
  • Make the most of your airline's flight rewards program and upgrade your seat. You can also bid for an upgrade in online auctions.

What is the best time to go to Cayman Islands?
Anytime is a fantastic time to go to Cayman Islands, though July, August and October are the busiest months. As with most places in the Northern Hemisphere, the summer starts June 20. If you'd prefer to spend your days in a light shirt than a winter jacket, this time of year may be ideal for you. Expect average daytime highs of 85 ºF and nighttime lows around 85 ºF.
Travel tips for Cayman Islands

  • Cayman Islands is full of amazing attractions and Playa Dorada is one of them. Lock in a car rental and head there at your leisure.
  • Seven Mile Beach offers tons of unique experiences and is an excellent place to start your adventure. Whether you're into cafés, restaurants, art or something else, this city will keep you on the go.

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.