$109 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 $109 One Way, $287 Round Trip

$287 return flights and $109 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.

Fri, Aug 21 - Tue, Aug 25

MIA

Miami

GCM

Grand Cayman

$287

Roundtrip

found 6 hours ago

Mon, Oct 12 - Sun, Oct 18

JFK

New York

GCM

Grand Cayman

$331

Roundtrip

just found

Wed, Nov 11 - Mon, Nov 16

BOS

Boston

GCM

Grand Cayman

$343

Roundtrip

found 6 days ago

Sat, Oct 17 - Sat, Oct 24

MIA

Miami

CYB

Cayman Brac

$350

Roundtrip

found 12 hours ago

Fri, Aug 14 - Mon, Aug 17

TPA

Tampa

GCM

Grand Cayman

$397

Roundtrip

just found

Fri, Aug 14 - Mon, Aug 17

MIA

Miami

LYB

Little Cayman

$399

Roundtrip

found 1 day ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
BOS	George Town	July 25 to July 27	$448
JFK	George Town	July 25 to July 30	$598
YYZ	George Town	July 25 to July 29	$963
ORD	George Town	July 25 to July 29	$2,085

*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

Aug 9 - Aug 10

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 ...

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

Fully refundable

$665 nightly

$744 total

Aug 17 - Aug 18

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! (1,000 reviews)

"We absolutely loved this hotel! Everyone was so friendly and welcoming. The beach was incredible and the facilities and room was amazing too. We will definitely come back!"

Reviewed on Jul 12, 2026

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Seven Mile Beach Seven Mile Beach Grand Cayman

$646 nightly

$731 total

Aug 16 - Aug 17

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 ...

9.2/10 Wonderful! (1,002 reviews)

"Resort and rooms were clean. The rooms are a little small and only offered two double beds for the 3 of us. Would have been nice to have more space and queen beds. Food was great and beach was amazing."

Reviewed on Jul 18, 2026

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

Grand Cayman Marriott Resort

389 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$344 nightly

$391 total

Aug 16 - Aug 17

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

Aug 9 - Aug 10

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 ...

Holiday Inn Resort Grand Cayman by IHG

278 Crighton Drive West Bay Grand Cayman

Fully refundable

$185 nightly

$205 total

Aug 5 - Aug 6

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! (680 reviews)

"I really love this property very relaxing the property is well kept.The location is beautiful. The room was comfortable. The view from my room is absolutely beautiful 😍room 2226 is everything only need to know thing is it’s located on the beach, but you’re not able to swim in the beach because it ..."

Reviewed on Jun 22, 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! (1,082 reviews)

"Clean room. Great service. Great view. Did not get my request for a ground ocean vs balcony ocean but that's OK."

Reviewed on Jul 19, 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

$248 nightly

$277 total

Aug 1 - Aug 2

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! (448 reviews)

"This resort is outstanding from the pool to the condos. The 2 bedroom condos feel like home! The location is excellent- we did not like Georgetown but didn’t mind a quick visit for the day. SMBR is minutes from Camana Bay, Cemetery Beach, Governor’s Beach, and not far from the Cayman Turtle Center. ..."

Reviewed on Jul 14, 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

Hotel Indigo Grand Cayman by IHG

32 Seafire Way Seven Mile Beach West Bay

$258 nightly

$289 total

Aug 14 - Aug 15

Total with taxes and fees

Book a stay at this luxury hotel in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 4 restaurants. Popular attractions Seven Mile Beach and Governor's ...

The Ritz-Carlton, Grand Cayman

West Bay Road Seven Mile Beach Grand Cayman

$767 nightly

$859 total

Aug 16 - Aug 17

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! (1,001 reviews)

"Beautiful property. Wish we could have stayed longer"

Reviewed on Jul 18, 2026

The Locale Hotel Grand Cayman

455 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$175 nightly

$198 total

Jul 28 - Jul 29

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! (1,004 reviews)

"Sarah at the front desk was amazing! We were late for our flight and the taxi was taking a while. She loaded up our family in her own vehicle and took us to the airport. We made it as the final boarding call was made and would have missed our flight if it wasn’t for her. We’re very grateful!"

Reviewed on Jul 19, 2026

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

Grand Cayman Marriott Resort

389 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$344 nightly

$391 total

Aug 16 - Aug 17

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.

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

$344 nightly

$391 total

Aug 16 - Aug 17

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

$665 nightly

$744 total

Aug 17 - Aug 18

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! (1,000 reviews)

"We absolutely loved this hotel! Everyone was so friendly and welcoming. The beach was incredible and the facilities and room was amazing too. We will definitely come back!"

Reviewed on Jul 12, 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 Governor's ...

9.8/10 Exceptional! (93 reviews)

"The property was wonderful. It is located in the perfect snorkeling location. The beach was amazing and you could do as much or as little as you like and be better for it. We needed to get away and reconnect and Aqua Bay was the perfect place to do that. I’m beyond grateful for the experience and ..."

Reviewed on Jul 14, 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! (1,082 reviews)

"Clean room. Great service. Great view. Did not get my request for a ground ocean vs balcony ocean but that's OK."

Reviewed on Jul 19, 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

Get the absolute lowest prices on flights to Cayman Islands by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

Book Your Flight To Cayman Islands Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Cayman Islands flights.

Avoid Check-In Hassles When Traveling On Flights to Cayman Islands

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Cayman Islands flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Cayman Islands flight using Orbitz.

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 $2,085. But it was jet-setters arriving in from Miami (MIA) who scored the top bargains. One-way tickets to Cayman Islands fell to just $109.

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.

$109 Cheap flights to Cayman Islands

Travelers

Top places to visit in Cayman Islands

Seven Mile Beach

West Bay

Cheap flights to Cayman Islands from $109 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 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

Hotel Indigo Grand Cayman by IHG

The Ritz-Carlton, Grand Cayman

The Locale Hotel Grand Cayman

Grand Cayman Marriott Resort

Family Friendly Hotels in Cayman Islands

Grand Cayman Marriott 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

Book Your Flight To Cayman Islands Using Your Mobile Device

Avoid Check-In Hassles When Traveling On Flights to Cayman Islands

Keeping Everyone Up To Date

Frequently asked questions

More to Explore

Rewards are waiting for you in the Orbitz app