$92 Cheap flights to Cayman Islands

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Many airlines offer flexible change policies

Top places to visit in Cayman Islands

A coastal city with a beach, clear blue waters, and a distant ship.

Seven Mile Beach

An aerial view of a coastal town with a large body of water, green hills, and a highway.

West Bay

Cheap flights to Cayman Islands from $92 One Way, $150 Round Trip

$150 return flights and $92 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 2 - Sat, Jan 2

GCM

Grand Cayman

CYB

Cayman Brac

$150

Roundtrip

found 3 days ago

Thu, May 13 - Thu, May 13

GCM

Grand Cayman

LYB

Little Cayman

$179

Roundtrip

found 8 hours ago

Sat, Oct 17 - Thu, Oct 22

MIA

Miami

GCM

Grand Cayman

$287

Roundtrip

found 11 hours ago

Sat, Feb 20 - Sat, Feb 27

MIA

Miami

CYB

Cayman Brac

$339

Roundtrip

found 6 hours ago

Tue, Nov 3 - Sat, Nov 7

LGA

New York

GCM

Grand Cayman

$351

Roundtrip

found 1 day ago

Sun, Dec 6 - Sat, Dec 12

EWR

New York

GCM

Grand Cayman

$351

Roundtrip

found 16 hours ago

Sun, Jan 31 - Sun, Feb 7

JFK

New York

GCM

Grand Cayman

$356

Roundtrip

found 12 hours ago

Fri, Nov 6 - Thu, Nov 12

BOS

Boston

GCM

Grand Cayman

$361

Roundtrip

found 2 days ago

Sat, Nov 7 - Thu, Nov 12

TPA

Tampa

GCM

Grand Cayman

$382

Roundtrip

found 4 days ago

Sat, Dec 12 - Wed, Dec 23

MIA

Miami

LYB

Little Cayman

$404

Roundtrip

found 6 days ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
EWR	George Town	October 16 to October 25	$479
BOS	George Town	October 16 to October 19	$606
YYZ	George Town	October 16 to October 21	$665
ORD	George Town	October 18 to October 29	$708

*Prices include taxes and fees

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

$258 nightly

$289 total

Oct 14 - Oct 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 ...

9/10 Wonderful! (1,004 reviews)

"Clean room. Get bed. Bathroom was clean."

Reviewed on Oct 12, 2026

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

Fully refundable

$755 nightly

$844 total

Oct 19 - Oct 20

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! (1,003 reviews)

"The rooms are nice. Gorgeous beach, pool and waterpark. Perfect if you have young kids. Also the library bar is a must do. The Spa is great too."

Reviewed on Oct 13, 2026

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Seven Mile Beach Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$579 nightly

$654 total

Oct 27 - Oct 28

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 ...

Save an average of 15% on thousands of hotels when you're signed in

Grand Cayman Marriott Beach Resort

389 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$363 nightly

$400 total

Oct 22 - Oct 23

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 ...

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

$258 nightly

$289 total

Oct 14 - Oct 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 ...

9/10 Wonderful! (1,004 reviews)

"Clean room. Get bed. Bathroom was clean."

Reviewed on Oct 12, 2026

Holiday Inn Resort Grand Cayman by IHG

278 Crighton Drive West Bay Grand Cayman

Fully refundable

$196 nightly

$217 total

Oct 16 - Oct 17

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 ...

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! (1,099 reviews)

"Hmmm…! Too much seaweed on the beach."

Reviewed on Oct 7, 2026

Get rates

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

$296 nightly

$331 total

Oct 14 - Oct 15

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! (458 reviews)

"On a fabulous beach, clean bathrooms, nice menu, comfy beach chairs with shade covers, beach service for bar/restaurant."

Reviewed on Oct 1, 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

The Ritz-Carlton, Grand Cayman

West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$922 nightly

$1,033 total

Oct 19 - Oct 20

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! (1,004 reviews)

"Beautiful view from our room and amazing staff!"

Reviewed on Oct 11, 2026

The Locale Hotel Grand Cayman

455 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$163 nightly

$186 total

Oct 15 - Oct 16

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! (1,007 reviews)

"I had a wonderful experience staying at Locale Hotel in George Town. The breakfast was included with our stay, and the à la carte breakfast was delicious and very good quality. The staff was super nice, friendly, and welcoming. A special thank you to the housekeeping ladies, who were absolutely amazing! ..."

Reviewed on Oct 12, 2026

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

Fully refundable

$755 nightly

$844 total

Oct 19 - Oct 20

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! (1,003 reviews)

"The rooms are nice. Gorgeous beach, pool and waterpark. Perfect if you have young kids. Also the library bar is a must do. The Spa is great too."

Reviewed on Oct 13, 2026

Save an average of 15% on thousands of hotels when you're signed in

Governors Village Seven Mile Beach Corridor

KY1-1206, Seven Mile Beach Corridor Seven Mile Beach Grand Cayman

Book a stay at this family-friendly hotel in Seven Mile Beach. Enjoy free parking, a 24-hour fitness center, and 2 meeting rooms. Popular attractions Seven Mile ...

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.

Family Friendly Hotels in Cayman Islands

Grand Cayman Marriott Beach Resort

389 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$363 nightly

$400 total

Oct 22 - Oct 23

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 ...

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

Fully refundable

$755 nightly

$844 total

Oct 19 - Oct 20

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! (1,003 reviews)

"The rooms are nice. Gorgeous beach, pool and waterpark. Perfect if you have young kids. Also the library bar is a must do. The Spa is great too."

Reviewed on Oct 13, 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 Camana ...

9.8/10 Exceptional! (95 reviews)

"Perfect stay. It is so sad that the place will be torn down. I was already dreaming of returning before the development."

Reviewed on Sep 25, 2026

Get rates

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! (1,099 reviews)

"Hmmm…! Too much seaweed on the beach."

Reviewed on Oct 7, 2026

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

4 people

Compact

Ford Focus

4 people

Midsize

Toyota Corolla

5 people

SUV

Jeep Compass

5 people

Cayman Islands

Start your search for cheap flights to Cayman Islands on Orbitz. Orbitz is where you will discover guaranteed low prices on Cayman Islands flights, as well as all of the following conveniences:

Travel Updates on Your Mobile Device

Orbitz offers cutting-edge mobile tools for your smartphone. Whether you own an iPhone or an Android phone, you can benefit from Orbitz’s flight status updates and even book your future Cayman Islands flights. You can also review and reserve hotel rooms for when your Cayman Islands flights land and see other special offers.

Low Prices Guaranteed on Flights to Cayman Islands

Orbitz offers large discounts on a wide range of Cayman Islands flights. Through our easy-to-use site, you can find, plan, and reserve your desired flights to Cayman Islands while taking advantage of the lowest fares around.

Customer Care When You Need It

Orbitz is dedicated to making your flight booking experience as stress-free as possible. If you need to cancel your reservation, you can do so at your own convenience by going to the Orbitz website. If you need to change your flights to Cayman Islands to another time or date, you can contact our customer service representatives by phone, and they help you make the flight adjustments you need.

Loyalty Program Participation Opportunities

Orbitz lets you add your loyalty or frequent flyer account numbers when you book qualifying flights to Cayman Islands. So don’t worry about missing out on earning miles or points simply because you aren’t booking with the airline directly. You can save on your flights, and rack up miles too.

Frequently asked questions

Which airlines fly to Cayman Islands?

Have a look at the deals from the 19 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 $150 and $708. But it was jet-setters arriving in from Grand Cayman (GCM) who scored the top bargains. One-way tickets to Cayman Islands fell to just $92.

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.

More to Explore

Car rentals near 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.

$92 Cheap flights to Cayman Islands

Top places to visit in Cayman Islands

Seven Mile Beach

West Bay

Cheap flights to Cayman Islands from $92 One Way, $150 Round Trip

Deals For This Weekend's Flights

Find The Perfect Hotel For After Your Flight

Score Epic Cayman Islands Accommodation Deals

The Sunshine Hotel and Suites

Kimpton Seafire Resort + Spa by IHG

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Grand Cayman Marriott Beach Resort

Our Top Cayman Islands Apartment Hotels

The Sunshine Hotel and Suites

Holiday Inn Resort Grand Cayman by IHG

The Reef Beach Resort, East End, Grand Cayman

Seven Mile Beach Resort & Club

Score Epic Cayman Islands Accommodation Deals

The Ritz-Carlton, Grand Cayman

The Locale Hotel Grand Cayman

Kimpton Seafire Resort + Spa by IHG

Governors Village Seven Mile Beach Corridor

Family Friendly Hotels in Cayman Islands

Grand Cayman Marriott Beach Resort

Kimpton Seafire Resort + Spa by IHG

Aqua Bay Club Condos

The Reef Beach Resort, East End, Grand Cayman

Need a Car For After Your Flight?

Economy

Compact

Midsize

SUV

Cayman Islands

Travel Updates on Your Mobile Device

Low Prices Guaranteed on Flights to Cayman Islands

Customer Care When You Need It

Loyalty Program Participation Opportunities

Frequently asked questions

More to Explore

Rewards are waiting for you in the Orbitz app