$95 Cheap flights to Cayman Islands

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Top places to visit in Cayman Islands

A coastal city with a beach, clear blue waters, and a distant ship.
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Seven Mile Beach

Seven Mile Beach
An aerial view of a coastal town with a large body of water, green hills, and a highway.
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FlightsFlights

West Bay

West Bay

Cheap flights to Cayman Islands from $95 One Way, $150 Round Trip

$150 return flights and $95 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, Oct 15 - Thu, Oct 15
GCM
Grand Cayman
CYB
Cayman Brac
$150 Roundtrip, found 4 days ago
$150
Roundtrip
found 4 days ago
Select Cayman Airways flight, departing Thu, Oct 15 from Grand Cayman to Cayman Brac, returning Thu, Oct 15, priced at $150 found 4 days ago
Tue, Jan 5 - Tue, Feb 2
GCM
Grand Cayman
CYB
Cayman Brac
$171 Roundtrip, found 10 hours ago
$171
Roundtrip
found 10 hours ago
Select Cayman Airways flight, departing Tue, Jan 5 from Grand Cayman to Cayman Brac, returning Tue, Feb 2, priced at $171 found 10 hours ago
Sat, Sep 26 - Mon, Sep 28
GCM
Grand Cayman
CYB
Cayman Brac
$173 Roundtrip, found 4 hours ago
$173
Roundtrip
found 4 hours ago
Select Cayman Airways flight, departing Sat, Sep 26 from Grand Cayman to Cayman Brac, returning Mon, Sep 28, priced at $173 found 4 hours ago
Sat, Oct 3 - Mon, Oct 5
GCM
Grand Cayman
CYB
Cayman Brac
$173 Roundtrip, found 4 hours ago
$173
Roundtrip
found 4 hours ago
Select Cayman Airways flight, departing Sat, Oct 3 from Grand Cayman to Cayman Brac, returning Mon, Oct 5, priced at $173 found 4 hours ago
Tue, Oct 6 - Tue, Oct 6
GCM
Grand Cayman
LYB
Little Cayman
$181 Roundtrip, found 5 days ago
$181
Roundtrip
found 5 days ago
Select Cayman Airways flight, departing Tue, Oct 6 from Grand Cayman to Little Cayman, returning Tue, Oct 6, priced at $181 found 5 days ago
Tue, Jan 5 - Tue, Feb 2
GCM
Grand Cayman
CYB
Cayman Brac
$183 Roundtrip, found 10 hours ago
$183
Roundtrip
found 10 hours ago
Select Cayman Airways flight, departing Tue, Jan 5 from Grand Cayman to Cayman Brac, returning Tue, Feb 2, priced at $183 found 10 hours ago
Thu, Dec 10 - Tue, Dec 15
LGA
New York
GCM
Grand Cayman
$334 Roundtrip, found 1 day ago
$334
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Dec 10 from New York to Grand Cayman, returning Tue, Dec 15, priced at $334 found 1 day ago
Thu, Dec 10 - Tue, Dec 15
EWR
New York
GCM
Grand Cayman
$334 Roundtrip, found 1 day ago
$334
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Dec 10 from New York to Grand Cayman, returning Tue, Dec 15, priced at $334 found 1 day ago
Sat, Oct 24 - Sat, Oct 31
BOS
Boston
GCM
Grand Cayman
$347 Roundtrip, found 1 day ago
$347
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Oct 24 from Boston to Grand Cayman, returning Sat, Oct 31, priced at $347 found 1 day ago
Mon, Dec 7 - Mon, Dec 14
IAD
Washington
GCM
Grand Cayman
$347 Roundtrip, found 7 hours ago
$347
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Mon, Dec 7 from Washington to Grand Cayman, returning Mon, Dec 14, priced at $347 found 7 hours ago
Sat, Oct 24 - Sat, Oct 31
ORD
Chicago
GCM
Grand Cayman
$347 Roundtrip, found 3 hours ago
$347
Roundtrip
found 3 hours ago
Select Air Canada flight, departing Sat, Oct 24 from Chicago to Grand Cayman, returning Sat, Oct 31, priced at $347 found 3 hours ago
Tue, Dec 1 - Fri, Dec 4
EWR
New York
GCM
Grand Cayman
$347 Roundtrip, just found
$347
Roundtrip
just found
Select Air Canada flight, departing Tue, Dec 1 from New York to Grand Cayman, returning Fri, Dec 4, priced at $347 just found
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
YYZGeorge TownSeptember 26 to October 1$259
ORDGeorge TownSeptember 25 to October 1$361
EWRGeorge TownSeptember 25 to September 28$361
BOSGeorge TownSeptember 26 to September 28$364
LHRGeorge TownSeptember 27 to September 30$1,592
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Cayman Islands Accommodation Deals

The Sunshine Hotel and Suites

The Sunshine Hotel and Suites

4 out of 5
1465 Esterley Tibbetts Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$258 nightly
The price is $289 total per night from Sep 22 to Sep 23
$289 total
Sep 22 - Sep 23
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! (1,000 reviews)
"The staff were excellent. Tip: Alexia and Ella are not the same person although they give the same excellent service. The rooms were clean. The restaurant had very good food and drinks and the staff was highly attentive. The pool was warm and clean every single day. I have absolutely no ..."

Reviewed on Sep 16, 2026

Opens in a new windowThe Sunshine Hotel and Suites
Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way Seven Mile Beach Grand Cayman
Fully refundable
$565 nightly
The price is $631 total per night from Sep 23 to Sep 24
$631 total
Sep 23 - Sep 24
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 ...
Opens in a new windowKimpton Seafire Resort + Spa by IHG
The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

4.5 out of 5
Seven Mile Beach Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$568 nightly
The price is $642 total per night from Oct 1 to Oct 2
$642 total
Oct 1 - Oct 2
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 ...
Opens in a new windowThe Westin Grand Cayman Seven Mile Beach Resort & Spa
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Grand Cayman Marriott Beach Resort.

Grand Cayman Marriott Beach Resort.

4.5 out of 5
389 West Bay Road Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$328 nightly
The price is $371 total per night from Oct 15 to Oct 16
$371 total
Oct 15 - Oct 16
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 ...
Opens in a new windowGrand Cayman Marriott Beach Resort.
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

The Sunshine Hotel and Suites

4 out of 5
1465 Esterley Tibbetts Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$258 nightly
The price is $289 total per night from Sep 22 to Sep 23
$289 total
Sep 22 - Sep 23
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! (1,000 reviews)
"The staff were excellent. Tip: Alexia and Ella are not the same person although they give the same excellent service. The rooms were clean. The restaurant had very good food and drinks and the staff was highly attentive. The pool was warm and clean every single day. I have absolutely no ..."

Reviewed on Sep 16, 2026

Opens in a new windowThe Sunshine Hotel and Suites
Holiday Inn Resort Grand Cayman by IHG

Holiday Inn Resort Grand Cayman by IHG

3.5 out of 5
278 Crighton Drive West Bay Grand Cayman
Fully refundable
$185 nightly
The price is $204 total per night from Oct 19 to Oct 20
$204 total
Oct 19 - Oct 20
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 ...
Opens in a new windowHoliday Inn Resort Grand Cayman by IHG
The Reef Beach Resort, East End, Grand Cayman

The Reef Beach Resort, East End, Grand Cayman

3.5 out of 5
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. ...
Get rates
Opens in a new windowThe Reef Beach Resort, East End, Grand Cayman
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Seven Mile Beach Resort & Club

Seven Mile Beach Resort & Club

3 out of 5
19 D Piper Way, West Bay Road Seven Mile Beach Grand Cayman
$275 nightly
The price is $308 total per night from Sep 22 to Sep 23
$308 total
Sep 22 - Sep 23
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 ...
Opens in a new windowSeven Mile Beach Resort & Club
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

The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
West Bay Road Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$760 nightly
The price is $859 total per night from Sep 22 to Sep 23
$859 total
Sep 22 - Sep 23
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. ...
Opens in a new windowThe Ritz-Carlton, Grand Cayman
Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way Seven Mile Beach Grand Cayman
Fully refundable
$565 nightly
The price is $631 total per night from Sep 23 to Sep 24
$631 total
Sep 23 - Sep 24
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 ...
Opens in a new windowKimpton Seafire Resort + Spa by IHG
The Locale Hotel Grand Cayman

The Locale Hotel Grand Cayman

3.5 out of 5
455 West Bay Road Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $191 total per night from Sep 23 to Sep 24
$191 total
Sep 23 - Sep 24
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 ...
Opens in a new windowThe Locale Hotel Grand Cayman
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Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
32 Seafire Way Seven Mile Beach West Bay
$339 nightly
The price is $379 total per night from Oct 1 to Oct 2
$379 total
Oct 1 - Oct 2
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! (901 reviews)
"We stayed in an ocean front room, the room was stunning and so was the view. The room was also very clean. Loved the fact that “Bonny moon beach club” chairs and umbrellas were included in our stay! I highly recommend staying here."

Reviewed on Sep 20, 2026

Opens in a new windowHotel Indigo Grand Cayman by IHG
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 Beach Resort.
Great for families

Grand Cayman Marriott Beach Resort.

4.5 out of 5
389 West Bay Road Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$328 nightly
The price is $371 total per night from Oct 15 to Oct 16
$371 total
Oct 15 - Oct 16
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 ...
Opens in a new windowGrand Cayman Marriott Beach Resort.
Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way Seven Mile Beach Grand Cayman
Fully refundable
$565 nightly
The price is $631 total per night from Sep 23 to Sep 24
$631 total
Sep 23 - Sep 24
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 ...
Opens in a new windowKimpton Seafire Resort + Spa by IHG
Aqua Bay Club Condos

Aqua Bay Club Condos

3 out of 5
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 ...
Get rates
Opens in a new windowAqua Bay Club Condos
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The Reef Beach Resort, East End, Grand Cayman

The Reef Beach Resort, East End, Grand Cayman

3.5 out of 5
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. ...
Get rates
Opens in a new windowThe Reef Beach Resort, East End, Grand Cayman
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
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Cayman Islands?
Have a look at the deals from the 24 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 $150 and $1,592. But it was jet-setters arriving in from Grand Cayman (GCM) who scored the top bargains. One-way tickets to Cayman Islands fell to just $95.
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

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.