$94 Cheap flights to Cayman Islands

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Top places to visit in Cayman Islands

panoramic landscape aerial view of the tropical paradise of the cayman islands in the caribbean sea

Seven Mile Beach

aerial drone footage of the island of grand cayman in the cayman islands in the clear blue and green tropical waters of the caribbean sea

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.

Mon, Jun 8 - Thu, Jun 11

MIA

Miami

GCM

Grand Cayman

$287

Roundtrip

just found

Sat, Aug 15 - Sat, Aug 22

BOS

Boston

GCM

Grand Cayman

$298

Roundtrip

found 5 hours ago

Sat, Jan 9 - Sat, Jan 16

JFK

New York

GCM

Grand Cayman

$299

Roundtrip

found 1 day ago

Tue, May 19 - Sat, May 23

EWR

New York

GCM

Grand Cayman

$303

Roundtrip

found 4 days ago

Tue, May 26 - Sat, May 30

LGA

New York

GCM

Grand Cayman

$313

Roundtrip

found 7 hours ago

Mon, Sep 7 - Thu, Sep 10

TPA

Tampa

GCM

Grand Cayman

$335

Roundtrip

found 11 hours ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
JFK	George Town	May 2 to May 4	$325
BOS	George Town	May 1 to May 4	$335
YYZ	George Town	May 1 to May 5	$462
YUL	George Town	May 2 to May 9	$505
JFK	West End	May 1 to May 7	$527
ORD	George Town	May 1 to May 4	$1,336

*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

$352 nightly

$393 total

May 3 - May 4

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)

Beautiful clean rooms. Comfy bed. Immaculate bathrooms. Friendly and helpful staff.

Reviewed on Apr 17, 2026

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

$1,046 nightly

$1,169 total

May 8 - May 9

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! (1,001 reviews)

The offer of another room after check out was appreciated to bridge the gap between checkout at airport , but the denial of spa facilities such as a team room and sauna unless I ponied up for “services” was inexplicable given that i was paying £1500 per night!

Reviewed on Apr 22, 2026

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Seven Mile Beach Seven Mile Beach Grand Cayman

$851 nightly

$952 total

May 10 - May 11

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! (1,003 reviews)

Staff was extremely friendly .

Reviewed on Apr 27, 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

$491 nightly

$549 total

May 21 - May 22

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)

Food was great. I would like to see a larger and more comfortable smoking are. Omar was great!

Reviewed on Apr 27, 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

$352 nightly

$393 total

May 3 - May 4

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)

Beautiful clean rooms. Comfy bed. Immaculate bathrooms. Friendly and helpful staff.

Reviewed on Apr 17, 2026

Holiday Inn Resort Grand Cayman by IHG

278 Crighton Drive West Bay Grand Cayman

Fully refundable

$259 nightly

$286 total

May 26 - May 27

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! (670 reviews)

Very nice facility with lots of amenities. The on-site restaurant was amazing with fantastic and reasonably priced food with a staff beyond compare. There is also an on-site water tour company and equipment rental place that run tours to Starfish Point and Stingray City from the dock on property. ...

Reviewed on Apr 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! (1,055 reviews)

Room was fantastic! Quiet area, but activities provided for those who wanted. Far from attractions but really great for a low key vacation. View from my room was amazing - so relaxing! Beach was a bit rough but I saw lots of people enjoying snorkelling. I made use of the spa and gym, and enjoyed ...

Reviewed on Apr 28, 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

$284 nightly

$321 total

May 1 - May 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! (427 reviews)

Good location with nice staff, but had difficulty using the TV and dryer. Also on Saturday could not reach the front desk after many tries. Beach access ok, but minimal support for guests. It is a good location for budget travel.

Reviewed on Apr 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.

Score Epic Cayman Islands Accommodation Deals

Hotel Indigo Grand Cayman by IHG

32 Seafire Way Seven Mile Beach West Bay

$446 nightly

$499 total

May 5 - May 6

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 Port of ...

9.8/10 Exceptional! (609 reviews)

Know the distance to the beach it’s a little walk but beautiful property!

Reviewed on Apr 25, 2026

Hampton by Hilton Grand Cayman Seven Mile Beach

22 Piper Way Seven Mile Beach

Fully refundableReserve now, pay when you stay

$291 nightly

$325 total

May 3 - May 4

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! (778 reviews)

Yes

Reviewed on Apr 25, 2026

Grand Cayman Marriott Resort

389 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$491 nightly

$549 total

May 21 - May 22

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)

Food was great. I would like to see a larger and more comfortable smoking are. Omar was great!

Reviewed on Apr 27, 2026

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

The Ritz-Carlton, Grand Cayman

West Bay Road Seven Mile Beach Grand Cayman

$1,251 nightly

$1,400 total

May 7 - May 8

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! (1,002 reviews)

Staff where so friendly and helpful.

Reviewed on Apr 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 Resort

389 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$491 nightly

$549 total

May 21 - May 22

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, close to beach

Travelers say...

Food was great. I would like to see a larger and more comfortable smoking are. Omar was great!

Reviewed on Apr 27, 2026

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

$1,046 nightly

$1,169 total

May 8 - May 9

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! (1,001 reviews)

Reviewed on Apr 22, 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 Port of ...

9.8/10 Exceptional! (90 reviews)

We stayed on the end condo on the ground floor. It was very clean and well stocked with comfy furnishings and amazing views! Claudette was so kind and helpful in the office along with the other girl. We sat in the screened in porch and watched the ocean and was able to snorkel right outside our condo. ...

Reviewed on Mar 1, 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! (1,055 reviews)

Reviewed on Apr 28, 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 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 11 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 $1,336. But it was jet-setters arriving in from Boston (BOS) 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 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

Hampton by Hilton Grand Cayman Seven Mile Beach

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

The Reef Beach Resort, East End, 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