What is the cheapest month to fly from Cayman Islands?

September is currently the cheapest month to fly from Cayman Islands . At this moment in time May is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

$189+ Flights from the Cayman Islands

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What to know about flights from Cayman Islands

Good round-trip deal	$137 or less
Good one-way deal	$246 or less

Price to beat on a round-trip flight from Cayman Islands.

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Price to beat on a one-way flight from Cayman Islands.

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Cheapest flights from Cayman Islands
Explore the most affordable flight options available from Cayman Islands. Find the lowest fares based on data from user searches, with prices last updated on July 29, 2025.

Mon 9/17:00 amGCM - MIA

Nonstop1h 40mCayman Airways

Mon 9/2911:00 amMIA - GCM

Nonstop1h 40mCayman Airways

Deal found 7/27$297

Sat 11/12:43 pmGCM - JFK

Nonstop3h 47mJetBlue

Mon 11/1010:30 amJFK - GCM

Nonstop4h 01mJetBlue

Deal found 7/28$317

Wed 9/1012:10 pmGCM - JFK

1 stop22h 56mAmerican Airlines

Wed 9/176:33 amJFK - GCM

1 stop5h 52mAmerican Airlines

Deal found 7/27$329

Wed 9/1012:10 pmGCM - EWR

1 stop9h 44mAmerican Airlines

Wed 9/176:05 amEWR - GCM

1 stop6h 20mAmerican Airlines

Deal found 7/27$332

Sat 10/258:25 amGCM - LGA

1 stop7h 48mAmerican Airlines

Fri 10/316:00 amLGA - GCM

1 stop6h 20mAmerican Airlines

Deal found 7/27$332

Sat 9/2012:10 pmGCM - MIA

Nonstop1h 36mAmerican Airlines

Wed 9/2410:30 amMIA - GCM

Nonstop1h 40mAmerican Airlines

Deal found 7/28$344

Fri 8/151:35 pmGCM - EWR

1 stop28h 47mUnited Airlines

Fri 8/227:29 pmEWR - GCM

1 stop18h 01mUnited Airlines

Deal found 7/27$353

Fri 8/151:35 pmGCM - LGA

1 stop8h 40mUnited Airlines

Fri 8/225:57 pmLGA - GCM

1 stop19h 33mUnited Airlines

Deal found 7/27$353

Wed 11/265:10 pmGCM - JFK

Nonstop3h 50mCayman Airways

Sun 11/3010:00 amJFK - GCM

Nonstop4h 00mCayman Airways

Deal found 7/27$355

Wed 9/1712:10 pmGCM - YYZ

1 stop10h 48mAmerican Airlines

Sat 9/206:14 amYYZ - GCM

1 stop6h 11mAmerican Airlines

Deal found 7/28$361

Tue 8/121:35 pmGCM - YYZ

2 stops19h 29mUnited Airlines

Sat 8/1611:00 amYYZ - GCM

2 stops26h 30mUnited Airlines

Deal found 7/28$365

Sat 10/1111:25 amGCM - TPA

Nonstop1h 50mCayman Airways

Sat 10/183:15 pmTPA - GCM

Nonstop1h 50mCayman Airways

Deal found 7/27$377

Best flights from Cayman Islands
Discover carefully curated flight deals from Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 29, 2025.

Mon 9/17:00 amGCM - MIA

Nonstop1h 40mCayman Airways

Mon 9/2911:00 amMIA - GCM

Nonstop1h 40mCayman Airways

Deal found 7/27$297

Sat 11/12:43 pmGCM - JFK

Nonstop3h 47mJetBlue

Mon 11/1010:30 amJFK - GCM

Nonstop4h 01mJetBlue

Deal found 7/28$317

Wed 9/1012:10 pmGCM - JFK

1 stop22h 56mAmerican Airlines

Wed 9/176:33 amJFK - GCM

1 stop5h 52mAmerican Airlines

Deal found 7/27$329

Fri 8/151:35 pmGCM - EWR

1 stop28h 47mUnited Airlines

Fri 8/227:29 pmEWR - GCM

1 stop18h 01mUnited Airlines

Deal found 7/27$353

Thu 9/1112:50 pmGCM - JFK

1 stop25h 18mMultiple Airlines

Thu 9/1811:45 amJFK - GCM

Nonstop4h 00mMultiple Airlines

Deal found 7/28$379

Fri 11/281:30 pmGCM - EWR

1 stop19h 48mAir Canada

Sat 11/296:55 pmEWR - GCM

1 stop17h 25mAir Canada

Deal found 7/27$398

Thu 9/1812:52 pmGCM - TPA

1 stop8h 06mDelta

Mon 9/226:00 amTPA - GCM

1 stop6h 36mDelta

Deal found 7/28$401

Tue 8/121:45 pmGCM - YYZ

Nonstop4h 09mWestJet

Sat 8/169:40 amYYZ - GCM

Nonstop4h 05mWestJet

Deal found 7/28$535

Sat 1/171:25 pmGCM - MCO

Nonstop1h 50mSouthwest

Tue 1/2011:00 amMCO - GCM

Nonstop1h 55mSouthwest

Deal found 7/27$541

Wed 9/1012:10 pmGCM - EWR

1 stop9h 44mAmerican Airlines

Wed 9/176:05 amEWR - GCM

1 stop6h 20mAmerican Airlines

Deal found 7/27$332

Fri 8/151:35 pmGCM - LGA

1 stop8h 40mUnited Airlines

Fri 8/225:57 pmLGA - GCM

1 stop19h 33mUnited Airlines

Deal found 7/27$353

Wed 11/265:10 pmGCM - JFK

Nonstop3h 50mCayman Airways

Sun 11/3010:00 amJFK - GCM

Nonstop4h 00mCayman Airways

Deal found 7/27$355

Last-minute flights from Cayman Islands
Discover last-minute flight deals departing from Cayman Islands. Data last updated July 29, 2025 and is based on user searches.

Sun 8/32:10 pmGCM - TPA

1 stop4h 27mAmerican Airlines

Sun 8/106:10 amTPA - GCM

1 stop6h 15mAmerican Airlines

Deal found 7/28$564

Tue 8/53:30 pmGCM - YYZ

1 stop20h 00mAmerican Airlines

Tue 8/123:45 pmYYZ - GCM

1 stop20h 35mAmerican Airlines

Deal found 7/29$453

Tue 8/52:10 pmGCM - EWR

1 stop9h 47mAmerican Airlines

Thu 8/146:00 amEWR - GCM

1 stop6h 25mAmerican Airlines

Deal found 7/27$512

Tue 8/52:10 pmGCM - LGA

1 stop8h 35mAmerican Airlines

Wed 8/137:59 pmLGA - GCM

1 stop16h 11mAmerican Airlines

Deal found 7/27$512

Tue 8/52:10 pmGCM - JFK

1 stop7h 40mAmerican Airlines

Thu 8/146:30 amJFK - GCM

1 stop5h 55mAmerican Airlines

Deal found 7/27$512

Tue 8/51:45 pmGCM - YYZ

Nonstop4h 09mWestJet

Tue 8/129:40 amYYZ - GCM

Nonstop4h 05mWestJet

Deal found 7/29$520

Thu 8/77:00 amGCM - EWR

1 stop13h 05mMultiple Airlines

Thu 8/145:30 amEWR - GCM

2 stops16h 50mMultiple Airlines

Deal found 7/27$545

Thu 8/77:00 amGCM - LGA

1 stop9h 30mMultiple Airlines

Tue 8/129:55 amLGA - GCM

1 stop7h 15mMultiple Airlines

Deal found 7/27$548

Fri 8/84:45 pmGCM - MIA

Nonstop1h 40mCayman Airways

Sat 8/2312:50 pmMIA - GCM

1 stop3h 00mCayman Airways

Deal found 7/27$346

Fri 8/84:45 pmGCM - MIA

Nonstop1h 40mMultiple Airlines

Sun 8/107:00 amMIA - GCM

1 stop6h 30mMultiple Airlines

Deal found 7/27$424

Fri 8/84:45 pmGCM - JFK

1 stop18h 02mMultiple Airlines

Wed 8/1312:44 pmJFK - GCM

1 stop23h 56mMultiple Airlines

Deal found 7/27$478

Fri 8/81:35 pmGCM - MIA

1 stop8h 04mUnited Airlines

Sun 8/107:00 amMIA - GCM

1 stop6h 30mUnited Airlines

Deal found 7/27$539

One-way flights from Cayman Islands
Search for one-way flight options from Cayman Islands. Find affordable one-way fares based on user searches. Data last updated July 29, 2025.

Tue 11/115:45 pmGCM - YYZ

2 stops27h 36mUnited Airlines

Deal found 7/27$189

Sun 8/174:45 pmGCM - MIA

Nonstop1h 40mCayman Airways

Deal found 7/28$197

Sun 8/2412:10 pmGCM - MIA

Nonstop1h 35mAmerican Airlines

Deal found 7/28$216

Sat 10/2511:45 amGCM - JFK

Nonstop3h 44mJetBlue

Deal found 7/29$218

Thu 9/412:50 pmGCM - EWR

1 stop10h 54mDelta

Deal found 7/28$224

Sat 11/85:30 pmGCM - LGA

1 stop6h 00mUnited Airlines

Deal found 7/27$224

Sat 11/85:10 pmGCM - JFK

Nonstop3h 50mCayman Airways

Deal found 7/27$227

Tue 8/192:10 pmGCM - LGA

1 stop8h 34mAmerican Airlines

Deal found 7/28$228

Tue 8/1912:25 pmGCM - JFK

1 stop8h 34mAmerican Airlines

Deal found 7/28$228

Thu 10/2312:50 pmGCM - JFK

1 stop8h 57mAir Canada

Deal found 7/26$230

Sat 1/242:15 pmGCM - JFK

Nonstop3h 52mDelta

Deal found 7/28$232

Tue 8/1912:25 pmGCM - EWR

1 stop20h 34mAmerican Airlines

Deal found 7/28$236

Fly to

Route

Depart

Return

Price

George TownMiami

GCM - MIA

GCMMIA

George Town Owen Roberts Intl

Mon 9/1

7:00 am-9:40 am

Nonstop1h 40m

Miami

Mon 9/29

11:00 am-11:40 am

Nonstop1h 40m

$297

George TownNew York

GCM - JFK

GCMJFK

George Town Owen Roberts Intl

Sat 11/1

2:43 pm-7:30 pm

Nonstop3h 47m

New York John F Kennedy Intl

Mon 11/10

10:30 am-2:31 pm

Nonstop4h 01m

$317

George TownNew York

GCM - JFK

GCMJFK

George Town Owen Roberts Intl

Wed 9/10

12:10 pm-12:06 pm

1 stop22h 56m

New York John F Kennedy Intl

Wed 9/17

6:33 am-11:25 am

1 stop5h 52m

$329

George TownNewark

GCM - EWR

GCMEWR

George Town Owen Roberts Intl

Wed 9/10

12:10 pm-10:54 pm

1 stop9h 44m

Newark

Wed 9/17

6:05 am-11:25 am

1 stop6h 20m

$332

George TownNew York

GCM - LGA

GCMLGA

George Town Owen Roberts Intl

Sat 10/25

8:25 am-5:13 pm

1 stop7h 48m

New York LaGuardia

Fri 10/31

6:00 am-11:20 am

1 stop6h 20m

$332

George TownMiami

GCM - MIA

GCMMIA

George Town Owen Roberts Intl

Sat 9/20

12:10 pm-2:46 pm

Nonstop1h 36m

Miami

Wed 9/24

10:30 am-11:10 am

Nonstop1h 40m

$344

George TownNewark

GCM - EWR

GCMEWR

George Town Owen Roberts Intl

Fri 8/15

1:35 pm-7:22 pm

1 stop28h 47m

Newark

Fri 8/22

7:29 pm-12:30 pm

1 stop18h 01m

$353

George TownNew York

GCM - LGA

GCMLGA

George Town Owen Roberts Intl

Fri 8/15

1:35 pm-11:15 pm

1 stop8h 40m

New York LaGuardia

Fri 8/22

5:57 pm-12:30 pm

1 stop19h 33m

$353

George TownNew York

GCM - JFK

GCMJFK

George Town Owen Roberts Intl

Wed 11/26

5:10 pm-9:00 pm

Nonstop3h 50m

New York John F Kennedy Intl

Sun 11/30

10:00 am-2:00 pm

Nonstop4h 00m

$355

George TownToronto

GCM - YYZ

GCMYYZ

George Town Owen Roberts Intl

Wed 9/17

12:10 pm-11:58 pm

1 stop10h 48m

Toronto Pearson Intl

Sat 9/20

6:14 am-11:25 am

1 stop6h 11m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 60 results

...

Best time to book a flight from Cayman Islands

Have a flexible travel schedule? Discover the best time to fly from Cayman Islands with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Cayman Islands

Get recent, data-driven insights about flights from Cayman Islands including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Cayman Islands?

Currently, September is the cheapest month in which you can book a flight from Cayman Islands (average of $112). Flying from Cayman Islands in May will prove the most costly (average of $382). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Cayman Islands?

For flights departing from Cayman Islands check dates and pricing for the following: JetBlue, Cayman Airways, American Airlines. These airlines depart to the following popular destinations: New York.

What is the cheapest place to fly to from Cayman Islands?

The cheapest city to fly to from Cayman Islands is Cayman Brac Gerrard-Smith, with prices starting at $136. Explore other affordable destinations below.

Cayman Brac Gerrard-Smith

Airline reviews for flights from Cayman Islands

Read through reviews of airlines servicing the Cayman Islands, such as Delta, JetBlue, and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,977 reviews

Reviews

1 / 20

10.0

Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!

Delta

8.0

Very good

7,977 reviews

Delta

8.0

Very good

7,977 reviews

Reviews

1 / 20

10.0

Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!

JetBlue

7.3

Good

2,913 reviews

Delta

8.0

Very good

7,977 reviews

Reviews

1 / 20

10.0

Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,977 reviews

Reviews

1 / 20

10.0

Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!

Air Canada

7.1

Good

9,822 reviews

Delta

8.0

Very good

7,977 reviews

Reviews

1 / 20

10.0

Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!

Browse thousands of different options on Cheapflights for your next trip

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Popular Round-Trip Flight Destinations

Flights from George Town to Miami

Flights from George Town to Charlotte

Flights from George Town to Nassau

Flights from George Town to Kingston

Flights from George Town to Atlanta

Flights from George Town to Tampa

Flights from George Town to Cayman Brac

Related info for your journey

What is the cheapest month to fly from Cayman Islands?
September is currently the cheapest month to fly from Cayman Islands. At this moment in time May is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

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Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/11. Fares are subject to change and may not be available on all flights or dates of travel.

What to know about flights from Cayman Islands

Good round-trip deal

Good one-way deal

Find flights from Cayman Islands

Cheapest flights from Cayman Islands
Explore the most affordable flight options available from Cayman Islands. Find the lowest fares based on data from user searches, with prices last updated on July 29, 2025.

Explore the most affordable flight options available from Cayman Islands. Find the lowest fares based on data from user searches, with prices last updated on July 29, 2025.

Best flights from Cayman Islands
Discover carefully curated flight deals from Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 29, 2025.

Discover carefully curated flight deals from Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 29, 2025.

Last-minute flights from Cayman Islands
Discover last-minute flight deals departing from Cayman Islands. Data last updated July 29, 2025 and is based on user searches.

Discover last-minute flight deals departing from Cayman Islands. Data last updated July 29, 2025 and is based on user searches.

One-way flights from Cayman Islands
Search for one-way flight options from Cayman Islands. Find affordable one-way fares based on user searches. Data last updated July 29, 2025.

Search for one-way flight options from Cayman Islands. Find affordable one-way fares based on user searches. Data last updated July 29, 2025.

Find flights from Cayman Islands within your budget

Best time to book a flight from Cayman Islands

Have a flexible travel schedule? Discover the best time to fly from Cayman Islands with our price prediction graph.

Travel insights for flights from Cayman Islands

Get recent, data-driven insights about flights from Cayman Islands including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Cayman Islands?

Which airlines fly from Cayman Islands?

What is the cheapest place to fly to from Cayman Islands?

Airline reviews for flights from Cayman Islands

Read through reviews of airlines servicing the Cayman Islands, such as Delta, JetBlue, and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly from Caribbean regions

Book your next flight out of one of these popular departure points located in Caribbean.

Fly from Cayman Islands cities

Consider departing from one of these cities also located in Cayman Islands. Flight origins are based on user searches made on Cheapflights and were last updated on July 29, 2025.

Popular international destinations from Cayman Islands

The most popular international flight routes departing from Cayman Islands we’ve come across at this time.

Popular Round-Trip Flight Destinations

Consider these popular destinations that Cheapflights users have chosen when departing from Cayman Islands. Routes are based on user searches and were last updated on July 29, 2025.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2025

Related info for your journey

What is the cheapest month to fly from Cayman Islands?

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$189+ Cheap flights from the Cayman Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/11. Fares are subject to change and may not be available on all flights or dates of travel.

What to know about flights from Cayman Islands

Good round-trip deal

Good one-way deal

Find flights from Cayman Islands

Cheapest flights from Cayman IslandsExplore the most affordable flight options available from Cayman Islands. Find the lowest fares based on data from user searches, with prices last updated on July 29, 2025.

Explore the most affordable flight options available from Cayman Islands. Find the lowest fares based on data from user searches, with prices last updated on July 29, 2025.

Find flights from Cayman Islands within your budget

Best time to book a flight from Cayman Islands

Have a flexible travel schedule? Discover the best time to fly from Cayman Islands with our price prediction graph.

Travel insights for flights from Cayman Islands

Get recent, data-driven insights about flights from Cayman Islands including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Cayman Islands?

Which airlines fly from Cayman Islands?

What is the cheapest place to fly to from Cayman Islands?

Airline reviews for flights from Cayman Islands

Read through reviews of airlines servicing the Cayman Islands, such as Delta, JetBlue, and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly from Caribbean regions

Book your next flight out of one of these popular departure points located in Caribbean.

Related info for your journey

What is the cheapest month to fly from Cayman Islands?

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Cayman Islands
Explore the most affordable flight options available from Cayman Islands. Find the lowest fares based on data from user searches, with prices last updated on July 29, 2025.