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Cayman Islands

$169+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — MIA
Oct 13 — Oct 201
Mon 10/13
Mon 10/20
1 adult, Economy
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What to know about flights from Cayman Islands

Discover essential information about flights departing from Cayman Islands, including flight schedules, destinations, airlines operating at the Cayman Islands airport, and any specific guidelines or requirements for travelers. Please note that the information is based on the most recent updates available. Data last updated September 13, 2025.

Good round-trip deal

$154 or less

Good one-way deal

$73 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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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 September 13, 2025.

Sun 10/191:35 pmGCM - YYZ
2 stops33h 23mUnited Airlines
Sat 10/257:47 pmYYZ - GCM
2 stops20h 43mUnited Airlines
Deal found 9/11$298
Fri 10/312:25 pmGCM - YYZ
1 stop9h 04mAmerican Airlines
Tue 10/76:00 amYYZ - GCM
1 stop6h 20mAmerican Airlines
Deal found 9/12$302
Fri 12/124:45 pmGCM - MIA
Nonstop1h 35mCayman Airways
Sun 12/1410:00 amMIA - GCM
Nonstop1h 35mCayman Airways
Deal found 9/12$305
Fri 10/104:45 pmGCM - MIA
Nonstop1h 35mCayman Airways
Sun 10/1211:00 amMIA - GCM
Nonstop1h 35mCayman Airways
Deal found 9/10$306
Fri 9/264:45 pmGCM - MIA
Nonstop1h 35mCayman Airways
Mon 9/2911:00 amMIA - GCM
Nonstop1h 35mCayman Airways
Deal found 9/12$307
Tue 10/2812:10 pmGCM - YYZ
2 stops21h 09mAmerican Airlines
Sun 11/25:00 amYYZ - GCM
1 stop8h 14mAmerican Airlines
Deal found 9/11$307
Sun 10/267:00 amGCM - MIA
Nonstop1h 35mCayman Airways
Sun 11/210:00 amMIA - GCM
Nonstop1h 35mCayman Airways
Deal found 9/11$308
Tue 10/2111:30 amGCM - MIA
Nonstop1h 35mCayman Airways
Fri 10/248:40 pmMIA - GCM
Nonstop1h 35mCayman Airways
Deal found 9/10$311
Tue 11/411:30 amGCM - MIA
Nonstop1h 35mCayman Airways
Fri 11/710:00 amMIA - GCM
Nonstop1h 35mCayman Airways
Deal found 9/11$313
Fri 1/167:00 amGCM - MIA
Nonstop1h 35mCayman Airways
Mon 1/1910:00 amMIA - GCM
Nonstop1h 35mCayman Airways
Deal found 9/12$316
Tue 9/3011:30 amGCM - MIA
Nonstop1h 35mCayman Airways
Thu 12/1110:00 amMIA - GCM
Nonstop1h 35mCayman Airways
Deal found 9/13$317
Sat 10/2511:45 amGCM - JFK
Nonstop3h 44mJetBlue
Fri 10/3110:35 amJFK - GCM
Nonstop3h 56mJetBlue
Deal found 9/11$319

Find flights from Cayman Islands within your budget

 
Find flights departing from Cayman Islands that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on September 13, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Miami

Route

Depart

Return

Price

George TownToronto

GCM - YYZ

GCMYYZ

George Town Owen Roberts Intl

Sun 10/19

1:35 pm-11:58 pm

2 stops33h 23m

Toronto Pearson Intl

Mon 10/27

6:10 am-3:30 pm

1 stop10h 20m

$298

George TownToronto

GCM - YYZ

GCMYYZ

George Town Owen Roberts Intl

Sun 10/12

1:35 pm-11:49 am

2 stops21h 14m

Toronto Pearson Intl

Fri 10/17

2:45 pm-12:30 pm

2 stops22h 45m

$298

George TownToronto

GCM - YYZ

GCMYYZ

George Town Owen Roberts Intl

Wed 12/24

2:50 pm-11:59 pm

1 stop9h 09m

Toronto Pearson Intl

Wed 12/31

11:00 am-4:00 pm

2 stops29h 00m

$298

George TownToronto

GCM - YYZ

GCMYYZ

George Town Owen Roberts Intl

Mon 10/27

4:45 pm-4:02 pm

2 stops22h 17m

Toronto Pearson Intl

Mon 11/3

7:40 pm-4:30 pm

2 stops20h 50m

$298

George TownToronto

GCM - YYZ

GCMYYZ

George Town Owen Roberts Intl

Thu 10/30

4:45 pm-2:20 pm

1 stop20h 35m

Toronto Pearson Intl

Mon 11/3

7:40 pm-4:30 pm

2 stops20h 50m

$298

George TownMiami

GCM - MIA

GCMMIA

George Town Owen Roberts Intl

Fri 9/26

4:45 pm-7:20 pm

Nonstop1h 35m

Miami

Mon 9/29

11:00 am-11:35 am

Nonstop1h 35m

$307

George TownToronto

GCM - YYZ

GCMYYZ

George Town Owen Roberts Intl

Sun 11/9

5:45 pm-9:21 pm

2 stops27h 36m

Toronto Pearson Intl

Mon 11/17

6:10 am-4:30 pm

1 stop10h 20m

$307

George TownMiami

GCM - MIA

GCMMIA

George Town Owen Roberts Intl

Fri 10/3

4:45 pm-7:20 pm

Nonstop1h 35m

Miami

Mon 10/6

8:40 pm-9:15 pm

Nonstop1h 35m

$312

George TownMiami

GCM - MIA

GCMMIA

George Town Owen Roberts Intl

Wed 12/10

11:30 am-1:05 pm

Nonstop1h 35m

Miami

Sun 12/14

10:00 am-11:35 am

Nonstop1h 35m

$317

George TownMiami

GCM - MIA

GCMMIA

George Town Owen Roberts Intl

Tue 9/30

11:30 am-2:05 pm

Nonstop1h 35m

Miami

Thu 12/11

10:00 am-11:35 am

Nonstop1h 35m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 60 results
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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, June is the cheapest month in which you can book a flight from Cayman Islands (average of $151). Flying from Cayman Islands in February will prove the most costly (average of $307). 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: Cayman Airways, American Airlines. These airlines depart to the following popular destinations: Miami.

Cayman Airways
Cayman Airways
From $136
American Airlines
American Airlines
From $264
United Airlines
United Airlines
From $160
British Airways
British Airways
From $383

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

The cheapest city to fly to from Cayman Islands is George Town Owen Roberts Intl, with prices starting at $73. Explore other affordable destinations below.

George Town Owen Roberts Intl
George Town Owen Roberts Intl
From $73
Cayman Brac Gerrard-Smith
Cayman Brac Gerrard-Smith
From $142
Panama City Tocumen Intl
Panama City Tocumen Intl
From $164
Houston Hobby
Houston Hobby
From $169

Airline reviews for flights from Cayman Islands

Read reviews and ratings of airlines operating flights from Cayman Islands. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Cayman Islands travel. Please note that the reviews are sourced from user searches and were last updated on September 13, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
Read through reviews of airlines servicing the Cayman Islands, such as 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.
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Boarding

7.5

Food

6.4

Crew

8.0

Comfort

7.2

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Boarding

7.5

Food

6.4

Crew

8.0

Comfort

7.2

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

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Related info for your journey

Access useful and relevant information related to your journey from Cayman Islands. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated September 13, 2025.

  • What is the cheapest month to fly from Cayman Islands?

    June is currently the cheapest month to fly from Cayman Islands. At this moment in time February 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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