$56 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 $56 One Way, $217 Round Trip

$217 return flights and $56 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 25 - Thu, Jan 29

ORD

Chicago

GCM

Grand Cayman

$217

Roundtrip

found 15 hours ago

Thu, Jan 22 - Sat, Jan 31

LGA

New York

GCM

Grand Cayman

$217

Roundtrip

found 2 days ago

Sat, Jan 31 - Sat, Feb 7

BOS

Boston

GCM

Grand Cayman

$217

Roundtrip

found 1 day ago

Sat, Jan 24 - Sat, Jan 31

EWR

New York

GCM

Grand Cayman

$217

Roundtrip

found 14 hours ago

Wed, Feb 4 - Fri, Feb 6

MIA

Miami

GCM

Grand Cayman

$247

Roundtrip

just found

Sun, Feb 8 - Fri, Feb 13

JFK

New York

GCM

Grand Cayman

$273

Roundtrip

found 4 days ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
LGA	George Town	January 18 to January 22	$256
YYZ	George Town	January 16 to January 20	$294
BOS	George Town	January 16 to January 24	$321
YUL	George Town	January 17 to January 20	$323
ORD	George Town	January 17 to January 27	$369
LHR	George Town	January 16 to February 1	$916

*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

Fully refundableReserve now, pay when you stay

$474 nightly

$530 total

Jan 24 - Jan 25

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 ...

8.8/10 Excellent! (1,002 reviews)

Clean room, great staff, steps away from the beach

Reviewed on Jan 9, 2026

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

$812 nightly

$908 total

Jan 25 - Jan 26

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! (977 reviews)

The restaurant staff is not very accommodating. They close early and don’t go out of their way for anything.

Reviewed on Jan 6, 2026

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Seven Mile Beach Seven Mile Beach Grand Cayman

$951 nightly

$1,063 total

Jan 12 - Jan 13

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 ...

9/10 Wonderful! (1,000 reviews)

Excellent all around! From the room and the service to the beach from. I will definitely be back.

Reviewed on Dec 28, 2025

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Grand Cayman Marriott Resort

389 West Bay Road Seven Mile Beach Grand Cayman

$616 nightly

$689 total

Jan 19 - Jan 20

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 ...

8.8/10 Excellent! (1,002 reviews)

My husband and i had a very enjoyable stay. The staff was so helpful and always had a great attitude going out of their way to make you feel special. We would love to come back someday and will tell our friends how great it was!

Reviewed on Jan 10, 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

Sunshine Suites Resort

1465 Esterley Tibbetts Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$474 nightly

$530 total

Jan 24 - Jan 25

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 ...

8.8/10 Excellent! (1,002 reviews)

Clean room, great staff, steps away from the beach

Reviewed on Jan 9, 2026

Holiday Inn Resort Grand Cayman by IHG

278 Crighton Drive West Bay Grand Cayman

Fully refundable

$471 nightly

$520 total

Jan 13 - Jan 14

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! (657 reviews)

Helpful staff and good amenities. Location is a bit out of the way which can be good if you want a more peaceful vacation. Not walking distance to anything but the staff is good at getting local taxi drivers when needed. Restaurant food is good and staff is very friendly.

Reviewed on Jan 1, 2026

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! (1,026 reviews)

Nice property! Great food! Very relaxing vacation!

Reviewed on Jan 2, 2026

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Seven Mile Beach Resort & Club

19 D Piper Way, West Bay Road Seven Mile Beach Grand Cayman

$383 nightly

$432 total

Jan 23 - Jan 24

Total with taxes and fees

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! (383 reviews)

Great stay!

Reviewed on Jan 5, 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

Hampton by Hilton Grand Cayman Seven Mile Beach

22 Piper Way Seven Mile Beach

Fully refundableReserve now, pay when you stay

$438 nightly

$490 total

Feb 2 - Feb 3

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! (676 reviews)

Excellent staff, clean rooms

Reviewed on Jan 8, 2026

Hotel Indigo Grand Cayman by IHG

32 Seafire Way Seven Mile Beach West Bay

$509 nightly

$569 total

Jan 13 - Jan 14

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 ...

9.6/10 Exceptional! (463 reviews)

Staff like Kadir was incredibly friendly and on top of his job. AC for a beach environment was great with no humidity in room after a hot day in the sun.

Reviewed on Jan 8, 2026

Grand Cayman Marriott Resort

389 West Bay Road Seven Mile Beach Grand Cayman

$616 nightly

$689 total

Jan 19 - Jan 20

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 ...

8.8/10 Excellent! (1,002 reviews)

My husband and i had a very enjoyable stay. The staff was so helpful and always had a great attitude going out of their way to make you feel special. We would love to come back someday and will tell our friends how great it was!

Reviewed on Jan 10, 2026

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The Grove

1350 W Bay Rd Seven Mile Beach West Bay

Book a stay at this luxury aparthotel in Seven Mile Beach. Enjoy free WiFi, free parking, and 3 restaurants. Popular attractions Seven Mile Beach and Port of ...

9.4/10 Exceptional! (67 reviews)

The building was brand new, which is nice, but it was a decent walk to the beach, which we did not expect and would have hoped the resort would’ve provided transportation to and from the beach. The Poling hot tub were a nice add-on to the rooftop and we enjoyed it each night. The beach area was never ...

Reviewed on Jan 6, 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.

Family Friendly Hotels in Cayman Islands

Grand Cayman Marriott Resort

389 West Bay Road Seven Mile Beach Grand Cayman

$689 total

per night

Jan 19 - Jan 20

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! (1,002 reviews)

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

Travelers say...

My husband and i had a very enjoyable stay. The staff was so helpful and always had a great attitude going out of their way to make you feel special. We would love to come back someday and will tell our friends how great it was!

Reviewed on Jan 10, 2026

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

$908 total

per night

Jan 25 - Jan 26

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! (977 reviews)

The restaurant staff is not very accommodating. They close early and don’t go out of their way for anything.

Reviewed on Jan 6, 2026

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! (1,026 reviews)

Nice property! Great food! Very relaxing vacation!

Reviewed on Jan 2, 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

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 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 $217 and $916. But it was jet-setters arriving in from Chicago (ORD) who scored the top bargains. One-way tickets to Cayman Islands fell to just $56.

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.

$56 Cheap flights to Cayman Islands

Top places to visit in Cayman Islands

Seven Mile Beach

West Bay

Cheap flights to Cayman Islands from $56 One Way, $217 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

Hotel Indigo Grand Cayman by IHG

Grand Cayman Marriott Resort

The Grove

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

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