$100 Cheap flights to Cayman Islands

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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 $100 One Way, $287 Round Trip

$287 return flights and $100 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.

Thu, Aug 13 - Tue, Aug 18

MIA

Miami

GCM

Grand Cayman

$287

Roundtrip

just found

Wed, Jun 10 - Sat, Jun 13

JFK

New York

GCM

Grand Cayman

$308

Roundtrip

found 2 days ago

Sat, Sep 19 - Thu, Sep 24

LGA

New York

GCM

Grand Cayman

$313

Roundtrip

found 14 hours ago

Mon, Nov 16 - Fri, Nov 20

EWR

New York

GCM

Grand Cayman

$313

Roundtrip

found 1 day ago

Tue, May 26 - Tue, Jun 2

TPA

Tampa

GCM

Grand Cayman

$327

Roundtrip

found 1 day ago

Sat, Jun 13 - Sat, Jun 20

MIA

Miami

CYB

Cayman Brac

$356

Roundtrip

found 1 day ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
LGA	George Town	May 24 to May 30	$355
BOS	George Town	May 24 to May 28	$438
ORD	George Town	May 24 to May 30	$445
LHR	George Town	May 22 to June 12	$1,448

*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 21 - May 22

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! (1,003 reviews)

"Good value with access to the Westin for beach. One bedroom suite did not have bedroom with a door - open floor plan which was unclear from photos & not ideal for our family. We had three people in a room which stated it accommodated four people and at 10 o’clock on our first night, we realized we ..."

Reviewed on May 20, 2026

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

$1,046 nightly

$1,169 total

Jun 20 - Jun 21

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)

"A truly impressive property and location on 7 mile beach. The staff from every aspect of the resort were so friendly, engaging, and personable. The restaurants were great, the beach is outstanding, and the view from the balcony was stunning. So happy we chose the Kimpton Seafire for our vacation ..."

Reviewed on May 19, 2026

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Seven Mile Beach Seven Mile Beach Grand Cayman

$798 nightly

$902 total

Jun 19 - Jun 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 6 restaurants. Our guests praise the helpful staff and the ...

9.2/10 Wonderful! (1,000 reviews)

"Room was clean. Noticed a sewage smell coming from the toilet, the whole time we were there. Seems like for the price this hotel could use some renovations. Was promised that I would get an ocean view room the day after I checked in. I went to front desk to check the following morning, and they told ..."

Reviewed on May 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

$402 nightly

$455 total

Jun 5 - Jun 6

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! (1,000 reviews)

"It was my first time in the Cayman Islands, and I overall enjoyed it. My boyfriend and I enjoyed staying at the Grand Cayman Marriott Resort. Our check-in and check-out process was smooth. It was my birthday, so my boyfriend had the room decorated, which was great. They also had a cake for me. The ..."

Reviewed on May 17, 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 21 - May 22

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! (1,003 reviews)

Reviewed on May 20, 2026

Holiday Inn Resort Grand Cayman by IHG

278 Crighton Drive West Bay Grand Cayman

Fully refundable

$235 nightly

$259 total

Jun 18 - Jun 19

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 ...

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! (1,068 reviews)

"Great Location Awesome Stay"

Reviewed on May 14, 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

$309 nightly

$346 total

May 21 - May 22

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! (435 reviews)

"Great location, steps from the beach. Lovely pool. Friendly helpful team and spacious clean apartments. Good restaurants a walk away. Highly recommended."

Reviewed on May 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.

Score Epic Cayman Islands Accommodation Deals

Hotel Indigo Grand Cayman by IHG

32 Seafire Way Seven Mile Beach West Bay

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! (644 reviews)

"Overall a fabulous hotel, clean and staff was fantastic and super friendly. My husband and I really enjoyed our stay. Bonus it's a short, easy walk to the best. Bata Bar by the pool surves not only the most picture perfect pina colada but best tasting too! Be sure to order one."

Reviewed on May 19, 2026

Get rates

Hampton by Hilton Grand Cayman Seven Mile Beach

22 Piper Way Seven Mile Beach

Fully refundableReserve now, pay when you stay

$232 nightly

$259 total

Jun 7 - Jun 8

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! (793 reviews)

"Wonderful property, staff, and great shuttle service"

Reviewed on May 20, 2026

Grand Cayman Marriott Resort

389 West Bay Road Seven Mile Beach Grand Cayman

Fully refundableReserve now, pay when you stay

$402 nightly

$455 total

Jun 5 - Jun 6

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! (1,000 reviews)

Reviewed on May 17, 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

$1,160 nightly

$1,298 total

Jun 17 - Jun 18

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! (1,000 reviews)

"."

Reviewed on May 17, 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

$402 nightly

$455 total

Jun 5 - Jun 6

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! (1,000 reviews)

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

Travelers say...

Reviewed on May 17, 2026

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

$1,046 nightly

$1,169 total

Jun 20 - Jun 21

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 May 19, 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 Cemetery ...

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! (1,068 reviews)

"Great Location Awesome Stay"

Reviewed on May 14, 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

Orbitz provides convenient, one-stop shopping for travelers looking for budget flights to Cayman Islands or any other low fare domestic or international air travel.

Innovative Orbitz Tools for the Trip Planner on the Move

Now it is even faster to find exclusive deals and book cheap Cayman Islands flights from any location with our new Orbitz apps. These cutting-edge mobile tools are available free to anyone with an Android device, iPad, or iPhone. Look up Cayman Islands's most popular attractions, best restaurants, and entertainment venues or check on your flights to Cayman Islands and make changes to your itinerary while waiting in line for your latte.

Stay on Budget, Earn Miles with Bargain Cayman Islands Flights

You can find amazing discount fares with Orbitz’s guaranteed low prices or take advantage of last-minute sales and special travel packages. You can also earn points towards your airline frequent flyer programs when you book qualified flights to Cayman Islands. That means you can rack up money-saving points and miles for future use while saving money now.

We Are Just a Phone Call Away If You Need Us

Booking, changing, or canceling your Cayman Islands flights is a breeze with Orbitz’s online and mobile tools, but that doesn't mean that we leave you hanging if you want to speak with one of our representatives. If you need help, just contact our Customer Service by email or phone. To enjoy a less stressful trip, be sure to sign up for instant alerts so we can send you any updates or delays relating to your flights to Cayman Islands to your mobile phone or email.

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 $1,448. But it was jet-setters arriving in from New York (EWR) who scored the top bargains. One-way tickets to Cayman Islands fell to just $100.

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.

$100 Cheap flights to Cayman Islands

Top places to visit in Cayman Islands

Seven Mile Beach

West Bay

Cheap flights to Cayman Islands from $100 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

Innovative Orbitz Tools for the Trip Planner on the Move

Stay on Budget, Earn Miles with Bargain Cayman Islands Flights

We Are Just a Phone Call Away If You Need Us

Frequently asked questions

More to Explore

Rewards are waiting for you in the Orbitz app