$63 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 $63 One Way, $233 Round Trip

$233 return flights and $63 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.

Sun, Jan 18 - Sat, Jan 31

ORD

Chicago

GCM

Grand Cayman

$233

Roundtrip

found 6 days ago

Wed, Feb 25 - Sun, Mar 1

MIA

Miami

GCM

Grand Cayman

$240

Roundtrip

found 4 days ago

Sun, Mar 8 - Thu, Mar 12

JFK

New York

GCM

Grand Cayman

$246

Roundtrip

found 8 hours ago

Sat, Jan 31 - Sat, Feb 7

BOS

Boston

GCM

Grand Cayman

$247

Roundtrip

found 3 days ago

Sat, Jan 10 - Thu, Jan 29

LGA

New York

GCM

Grand Cayman

$253

Roundtrip

found 4 days ago

Fri, Mar 6 - Wed, Mar 11

EWR

New York

GCM

Grand Cayman

$256

Roundtrip

found 1 day ago

Tue, Feb 3 - Sat, Feb 7

DCA

Washington

GCM

Grand Cayman

$296

Roundtrip

found 6 hours ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
YYZ	George Town	December 19 to December 25	$381
ORD	George Town	December 21 to December 24	$452
LGA	George Town	December 20 to December 25	$473
BOS	George Town	December 20 to December 27	$516
LHR	George Town	December 19 to December 31	$1,299
EWR	West End	December 20 to December 28	$1,437
EWR	Little Cayman	December 20 to December 28	$1,456
BKK	George Town	December 20 to December 27	$2,148
FCO	George Town	December 19 to January 11	$2,387

*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

$406 total

per night

Dec 17 - Dec 18

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! (1,001 reviews)

Newly renovated. Clean rooms. Pool and restaurant wasn’t open but we had full access to the Westin facilities where we spent the day, which was great!

Reviewed on Dec 8, 2025

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

$988 total

per night

Jan 4 - Jan 5

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! (967 reviews)

The staff and service was excellent.

Reviewed on Dec 14, 2025

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Seven Mile Beach Seven Mile Beach Grand Cayman

$828 total

per night

Dec 17 - Dec 18

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

$470 total

per night

Dec 17 - Dec 18

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! (1,004 reviews)

Staff was very friendly and helpful

Reviewed on Dec 13, 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

$406 total

per night

Dec 17 - Dec 18

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! (1,001 reviews)

Newly renovated. Clean rooms. Pool and restaurant wasn’t open but we had full access to the Westin facilities where we spent the day, which was great!

Reviewed on Dec 8, 2025

Holiday Inn Resort Grand Cayman by IHG

278 Crighton Drive West Bay Grand Cayman

$327 total

per night

Dec 18 - Dec 19

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! (653 reviews)

Everyone we encountered was great. They proactively asked if we needed anything. Dinner by the pool was fun, as there was live music. The food was very good.

Reviewed on Dec 14, 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

$324 total

per night

Dec 18 - Dec 19

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! (373 reviews)

We moved to this resort after spending a week on the east end! We absolutely loved it. Although the beach us non existent, its not hard or far to get to good beach! The front desk staff was amazing and very helpful! The only set back was our safe didn't work nor the living room tv, but both very ...

Reviewed on Dec 11, 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

$348 total

per night

Dec 18 - Dec 19

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! (651 reviews)

ThI staying experience is superb

Reviewed on Dec 14, 2025

Grand Cayman Marriott Resort

389 West Bay Road Seven Mile Beach Grand Cayman

$470 total

per night

Dec 17 - Dec 18

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! (1,004 reviews)

Staff was very friendly and helpful

Reviewed on Dec 13, 2025

Hotel Indigo Grand Cayman by IHG

32 Seafire Way Seven Mile Beach West Bay

$586 total

per night

Dec 17 - Dec 18

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 ...

9.6/10 Exceptional! (445 reviews)

Amazing place to stay in grand cayman . Great stay for families as well. Every single detail of your stay will be taken care of. Highly recommend. Definitely rent a car if you’re comfortable though since you’re limited to local establishments and have to take public transport or taxis

Reviewed on Dec 10, 2025

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The Locale Hotel Grand Cayman

455 West Bay Road Seven Mile Beach Grand Cayman

$245 total

per night

Dec 17 - Dec 18

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! (1,002 reviews)

All good

Reviewed on Dec 13, 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

$470 total

per night

Dec 17 - Dec 18

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! (1,004 reviews)

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

Travelers say...

Staff was very friendly and helpful

Reviewed on Dec 13, 2025

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

$988 total

per night

Jan 4 - Jan 5

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! (967 reviews)

The staff and service was excellent.

Reviewed on Dec 14, 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

Frequently asked questions

Which airlines fly to Cayman Islands?

Have a look at the deals from the 14 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 $233 and $2,387. But it was jet-setters arriving in from Miami (MIA) who scored the top bargains. One-way tickets to Cayman Islands fell to just $63.

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.

$63 Cheap flights to Cayman Islands

Travelers

Top places to visit in Cayman Islands

Seven Mile Beach

West Bay

Cheap flights to Cayman Islands from $63 One Way, $233 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

Grand Cayman Marriott Resort

Hotel Indigo Grand Cayman by IHG

The Locale Hotel 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

Frequently asked questions

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