$61 Cheap flights to Cayman Islands

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Top places to visit in Cayman Islands

Seven Mile Beach

West Bay

Cheap flights to Cayman Islands from $61 One Way, $237 Round Trip

$237 return flights and $61 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.

Sat, Jan 17 - Sat, Feb 7

LGA

New York

GCM

Grand Cayman

$237

Roundtrip

found 6 days ago

Thu, Jan 29 - Sat, Feb 7

ORD

Chicago

GCM

Grand Cayman

$241

Roundtrip

found 5 days ago

Fri, Jan 2 - Wed, Jan 7

MIA

Miami

GCM

Grand Cayman

$246

Roundtrip

just found

Sat, Jan 31 - Sat, Feb 7

EWR

New York

GCM

Grand Cayman

$255

Roundtrip

just found

Thu, Feb 26 - Thu, Mar 5

JFK

New York

GCM

Grand Cayman

$256

Roundtrip

found 5 days ago

Sat, Jan 17 - Sat, Jan 24

BOS

Boston

GCM

Grand Cayman

$270

Roundtrip

found 3 hours ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
BOS	George Town	December 14 to December 20	$323
LGA	George Town	December 14 to December 18	$332
YYZ	George Town	December 13 to December 24	$369
ORD	George Town	December 14 to December 16	$461
JFK	Little Cayman	December 14 to December 24	$541
JFK	West End	December 14 to December 21	$542
LHR	George Town	December 12 to December 16	$1,543

*Prices include taxes and fees

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

$363 nightly

$406 total

Dec 14 - Dec 15

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)

We actually stayed at the Westin because sunshine suites is still being renovated. The westin was fabulous!!

Reviewed on Nov 20, 2025

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

$753 nightly

$841 total

Dec 12 - Dec 13

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! (960 reviews)

Very clean room, friendly staff and pristine beach with many complimentary water amenities for guests.

Reviewed on Nov 30, 2025

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Seven Mile Beach Seven Mile Beach Grand Cayman

$684 nightly

$766 total

Dec 15 - Dec 16

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! (1,000 reviews)

Clean rooms, very nice staff

Reviewed on Nov 17, 2025

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Grand Cayman Marriott Resort

389 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$552 nightly

$617 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! (1,000 reviews)

Great staff, location, clean

Reviewed on Nov 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.

Our Top Cayman Islands Apartment Hotels

Sunshine Suites Resort

1465 Esterley Tibbetts Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$363 nightly

$406 total

Dec 14 - Dec 15

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)

We actually stayed at the Westin because sunshine suites is still being renovated. The westin was fabulous!!

Reviewed on Nov 20, 2025

Holiday Inn Resort Grand Cayman by IHG

278 Crighton Drive West Bay Grand Cayman

Fully refundable

$314 nightly

$346 total

Dec 19 - Dec 20

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! (650 reviews)

Good staff

Reviewed on Nov 12, 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! (1,017 reviews)

Our family had a wonderful stay. All rooms have a beach view that is magnificent. Staff is friendly and helpful. We found lounge chairs and shade everyday we went to the beach.

Reviewed on Nov 18, 2025

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Seven Mile Beach Resort & Club

19 D Piper Way, West Bay Road Seven Mile Beach Grand Cayman

$291 nightly

$327 total

Dec 14 - Dec 15

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! (369 reviews)

Very nice

Reviewed on Nov 22, 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

$303 nightly

$339 total

Dec 15 - Dec 16

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! (639 reviews)

Yes to all

Reviewed on Dec 2, 2025

The Locale Hotel Grand Cayman

455 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$240 nightly

$270 total

Dec 14 - Dec 15

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! (1,000 reviews)

Right by the beach. The room was cleaned daily! Amazing front desk service and all staff was so kind and helpful.

Reviewed on Dec 1, 2025

Grand Cayman Marriott Resort

389 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$552 nightly

$617 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! (1,000 reviews)

Great staff, location, clean

Reviewed on Nov 18, 2025

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The Ritz-Carlton, Grand Cayman

West Bay Road Seven Mile Beach Grand Cayman

$1,031 nightly

$1,154 total

Dec 9 - Dec 10

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! (1,000 reviews)

The room, staff, amenities and beach were formidable. We stayed there for 14 days. We are especially thankful for Xavior at the front desk, Tania, Irene, and Mohamed in the restaurant. We were also impressed by Uli and Jonathan at the tennis court. Phil

Reviewed on Nov 28, 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

Fully refundableReserve now, pay when you stay

$552 nightly

$617 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! (1,000 reviews)

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

Travelers say...

Great staff, location, clean

Reviewed on Nov 18, 2025

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

$753 nightly

$841 total

Dec 12 - Dec 13

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! (960 reviews)

Very clean room, friendly staff and pristine beach with many complimentary water amenities for guests.

Reviewed on Nov 30, 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

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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! (1,017 reviews)

Our family had a wonderful stay. All rooms have a beach view that is magnificent. Staff is friendly and helpful. We found lounge chairs and shade everyday we went to the beach.

Reviewed on Nov 18, 2025

Get rates

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

4 people

Compact

Ford Focus or similar

4 people

Midsize

Toyota Corolla or similar

5 people

SUV

Jeep Compass or similar

5 people

Cayman Islands

Finding cheap flights to Cayman Islands is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Cayman Islands flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Cayman Islands through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Cayman Islands—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Cayman Islands flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Cayman Islands with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

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 $237 and $1,543. But it was jet-setters arriving in from New York (LGA) who scored the top bargains. One-way tickets to Cayman Islands fell to just $61.

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.

$61 Cheap flights to Cayman Islands

Top places to visit in Cayman Islands

Seven Mile Beach

West Bay

Cheap flights to Cayman Islands from $61 One Way, $237 Round Trip

Deals For This Weekend's Flights

Find The Perfect Hotel For After Your Flight

Score Epic Cayman Islands Accommodation Deals

Sunshine Suites Resort

Kimpton Seafire Resort + Spa by IHG

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Grand Cayman Marriott Resort

Our Top Cayman Islands Apartment Hotels

Sunshine Suites Resort

Holiday Inn Resort Grand Cayman by IHG

Wyndham Reef Resort Grand Cayman

Seven Mile Beach Resort & Club

Score Epic Cayman Islands Accommodation Deals

Hampton by Hilton Grand Cayman Seven Mile Beach

The Locale Hotel Grand Cayman

Grand Cayman Marriott Resort

The Ritz-Carlton, Grand Cayman

Family Friendly Hotels in Cayman Islands

Grand Cayman Marriott Resort

Kimpton Seafire Resort + Spa by IHG

Aqua Bay Club Condos

Wyndham Reef Resort Grand Cayman

Need a Car For After Your Flight?

Economy

Compact

Midsize

SUV

Cayman Islands

Mobile Site and Apps

Pick and Choose or Book Full Vacation Packages

Rewards That Are Miles Better

Great Deals Every Day

Frequently asked questions

More to Explore

Rewards are waiting for you in the Orbitz app