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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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — MIA
May 21 — May 281
Thu 5/21
Thu 5/28
1 adult, Economy
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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 April 21, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

George TownMiami

GCM - MIA

GCMMIA

George Town Owen Roberts Intl

Sat 5/30

4:07 pm-6:44 pm

Nonstop1h 37m

Miami

Sat 6/6

10:15 am-10:55 am

Nonstop1h 40m

$287

George TownNew York

GCM - LGA

GCMLGA

George Town Owen Roberts Intl

Sat 6/13

1:50 pm-11:10 pm

1 stop8h 20m

New York LaGuardia

Mon 6/15

6:00 am-12:30 pm

1 stop7h 30m

$304

George TownNew York

GCM - LGA

GCMLGA

George Town Owen Roberts Intl

Wed 6/10

1:35 pm-11:15 pm

1 stop8h 40m

New York LaGuardia

Mon 6/15

6:00 am-12:30 pm

1 stop7h 30m

$304

George TownMiami

GCM - MIA

GCMMIA

George Town Owen Roberts Intl

Tue 6/2

1:19 pm-9:18 pm

1 stop6h 59m

Miami

Tue 6/9

6:00 am-11:34 am

1 stop6h 34m

$335

George TownNew York

GCM - LGA

GCMLGA

George Town Owen Roberts Intl

Thu 4/30

1:35 pm-8:57 pm

1 stop30h 22m

New York LaGuardia

Tue 5/5

2:10 pm-12:30 pm

2 stops23h 20m

$338

George TownNewark

GCM - EWR

GCMEWR

George Town Owen Roberts Intl

Sat 9/12

1:35 pm-12:51 am

1 stop10h 16m

Newark

Sat 9/19

6:00 am-12:25 pm

1 stop7h 25m

$339

George TownNew York

GCM - LGA

GCMLGA

George Town Owen Roberts Intl

Fri 10/16

12:40 pm-11:30 pm

1 stop9h 50m

New York LaGuardia

Tue 10/20

7:45 am-6:06 pm

1 stop11h 21m

$378

George TownTampa

GCM - TPA

GCMTPA

George Town Owen Roberts Intl

Wed 6/3

1:19 pm-10:22 pm

1 stop8h 03m

Tampa

Wed 6/10

5:20 am-11:34 am

1 stop7h 14m

$380

George TownNew York

GCM - JFK

GCMJFK

George Town Owen Roberts Intl

Thu 4/30

12:35 pm-7:27 am

2 stops17h 52m

New York John F Kennedy Intl

Mon 5/11

7:29 pm-11:00 am

2 stops16h 31m

$381

George TownToronto

GCM - YYZ

GCMYYZ

George Town Owen Roberts Intl

Mon 5/4

1:35 pm-3:46 pm

2 stops25h 11m

Toronto Pearson Intl

Wed 5/6

7:43 pm-12:30 pm

2 stops17h 47m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/20

Showing 1-10 of 60 resultsSorted by cheapest first
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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, November is the cheapest month in which you can book a flight from Cayman Islands (average of $113). Flying from Cayman Islands in September will prove the most costly (average of $248). 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 $113
American Airlines
American Airlines
From $245
WestJet
WestJet
From $155
Air Canada
Air Canada
From $180

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 $116. Explore other affordable destinations below.

Cayman Brac Gerrard-Smith
Cayman Brac Gerrard-Smith
From $116
Nassau Intl
Nassau Intl
From $157
Fort Lauderdale
Fort Lauderdale
From $165
Washington, D.C.
Washington, D.C.
From $168

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 April 21, 2026. 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
7.1
Good
11,645 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Overall

7.1

Crew

7.9

Food

6.4

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,645 reviews
American Airlines
7.1
Good
11,645 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Overall

7.1

Crew

7.9

Food

6.4

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

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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 April 21, 2026.

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

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