$94 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 $94 One Way, $287 Round Trip

$287 return flights and $94 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.

Tue, Feb 2 - Tue, Mar 2

MIA

Miami

GCM

Grand Cayman

$287

Roundtrip

found 1 day ago

Sat, Dec 5 - Sat, Dec 12

MIA

Miami

CYB

Cayman Brac

$338

Roundtrip

found 7 hours ago

Tue, Dec 1 - Tue, Dec 8

LGA

New York

GCM

Grand Cayman

$351

Roundtrip

found 1 day ago

Sun, Apr 18 - Fri, Apr 23

JFK

New York

GCM

Grand Cayman

$351

Roundtrip

found 21 hours ago

Tue, Jun 29 - Thu, Jul 8

EWR

New York

GCM

Grand Cayman

$351

Roundtrip

just found

Mon, May 31 - Fri, Jun 4

BOS

Boston

GCM

Grand Cayman

$364

Roundtrip

found 2 days ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
YUL	George Town	November 1 to November 2	$314
YYZ	George Town	November 1 to November 8	$318
ORD	George Town	October 30 to November 1	$455
EWR	George Town	October 30 to November 4	$455

*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 28 - Oct 29

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! (1,001 reviews)

"We loved our clean, comfortable and modern room. It had all the amenities we needed. We pared directly in front of our room. Staff were amazing and helpful."

Reviewed on Oct 23, 2026

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

Fully refundable

$721 nightly

$806 total

Oct 28 - Oct 29

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! (1,004 reviews)

"The best stay ever"

Reviewed on Oct 26, 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 28 - Oct 29

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

$391 nightly

$433 total

Oct 28 - Oct 29

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! (1,003 reviews)

"Great location and easy to get to from airport. Loved the beach and pool area. The attendants were very helpful with making sure you had umbrellas if you wanted shade. We ate at the pool/beach grill for an early dinner and that was very good as well. I thought food and drinks were on the expensive ..."

Reviewed on Oct 26, 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

$258 nightly

$289 total

Oct 28 - Oct 29

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! (1,001 reviews)

"We loved our clean, comfortable and modern room. It had all the amenities we needed. We pared directly in front of our room. Staff were amazing and helpful."

Reviewed on Oct 23, 2026

Holiday Inn Resort Grand Cayman by IHG

278 Crighton Drive West Bay Grand Cayman

Fully refundable

$209 nightly

$230 total

Oct 31 - Nov 1

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! (702 reviews)

"Best biscuit and gravy I've had in years. Excellent Child friendly. Clean and quiet."

Reviewed on Oct 24, 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! (1,102 reviews)

"Loved the walkout except at night when sound travelled into the unit from the pool, adjoining decks like they were in the building. Linens could be improved….old, poor quality. Great people/staff. Stay here often because of them."

Reviewed on Oct 26, 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 28 - Oct 29

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 ...

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

$913 nightly

$1,033 total

Oct 28 - Oct 29

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. ...

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

Fully refundable

$721 nightly

$806 total

Oct 28 - Oct 29

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! (1,004 reviews)

"The best stay ever"

Reviewed on Oct 26, 2026

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 ...

9.6/10 Exceptional! (492 reviews)

"Great location. Short walk to the beach. Apartment was beautiful and well equipped Would absolutely stay here again"

Reviewed on Oct 26, 2026

Get rates

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

$391 nightly

$433 total

Oct 28 - Oct 29

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! (1,003 reviews)

Reviewed on Oct 26, 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 Beach Resort

389 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$391 nightly

$433 total

Oct 28 - Oct 29

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! (1,003 reviews)

Families like: Outdoor pool, kids club, babysitting, on the beach

Travelers say...

Reviewed on Oct 26, 2026

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

Fully refundable

$721 nightly

$806 total

Oct 28 - Oct 29

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! (1,004 reviews)

"The best stay ever"

Reviewed on Oct 26, 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! (1,102 reviews)

Reviewed on Oct 26, 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

Snag some “suite” deals when you add cheap hotel rooms to Cayman Islands flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

Budget Prices, Luxury Life

Find mobile-only bargains on your home away from home with Orbitz cutting-edge mobile tools. Search domestic and international hotels at Orbitz On the Go. Find free travel planning apps for your iPhone, Android or iPad. You’ll always get our guaranteed low prices on your favorite hotels and flights to Cayman Islands.

Fun for All

While shopping Orbitz sales on Cayman Islands flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.

Non-Stop or Stop and Visit

Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Cayman Islands flights, you will always find the best air travel prices at Orbitz.

All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Cayman Islands. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

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 $455. But it was jet-setters arriving in from Miami (MIA) who scored the top bargains. One-way tickets to Cayman Islands fell to just $94.

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.

$94 Cheap flights to Cayman Islands

Top places to visit in Cayman Islands

Seven Mile Beach

West Bay

Cheap flights to Cayman Islands from $94 One Way, $287 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

Kimpton Seafire Resort + Spa by IHG

Governors Village Seven Mile Beach Corridor

Grand Cayman Marriott Beach Resort

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

Budget Prices, Luxury Life

Fun for All

Non-Stop or Stop and Visit

All in One

Frequently asked questions

More to Explore

Rewards are waiting for you in the Orbitz app