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Cheap flights from Portland, Maine to the Cayman Islands from $137

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland, Maine to the Cayman Islands departing on 4/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Portland, Maine to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:50 pm - 1:10 pm
PWM
-
GCM
19h 20m
2 stops
American Airlines Logo
1:20 pm - 11:31 am
GCM
-
PWM
21h 11m
2 stops
$350American Airlines
Sun, Sep 6 - Sat, Sep 12
American Airlines Logo
6:01 pm - 11:31 am
PWM
-
GCM
18h 30m
2 stops
American Airlines Logo
2:10 pm - 11:15 am
GCM
-
PWM
20h 05m
2 stops
$450American Airlines
Thu, Apr 30 - Thu, May 7
American Airlines Logo
6:54 pm - 11:01 am
PWM
-
GCM
17h 07m
2 stops
American Airlines Logo
5:12 pm - 2:24 pm
GCM
-
PWM
20h 12m
2 stops
$455American Airlines
Wed, Jun 10 - Fri, Jun 19
American Airlines Logo
11:57 am - 11:25 am
PWM
-
GCM
24h 28m
1 stop
American Airlines Logo
1:20 pm - 11:31 am
GCM
-
PWM
21h 11m
2 stops
$461American Airlines
Sun, Sep 6 - Sat, Sep 12
Delta Logo
6:00 am - 11:34 am
PWM
-
GCM
6h 34m
1 stop
Delta Logo
12:59 pm - 11:15 pm
GCM
-
PWM
9h 16m
1 stop
$493Delta
Wed, Jun 10 - Fri, Jun 19
American Airlines Logo
5:57 pm - 11:01 am
PWM
-
GCM
18h 04m
2 stops
American Airlines Logo
12:33 pm - 10:47 pm
GCM
-
PWM
9h 14m
1 stop
$550American Airlines
Sun, Jun 14 - Wed, Jun 17
American Airlines Logo
5:57 pm - 11:30 am
PWM
-
GCM
18h 33m
1 stop
American Airlines Logo
5:12 pm - 2:24 pm
GCM
-
PWM
20h 12m
2 stops
$566American Airlines
Wed, Jun 10 - Fri, Jun 19
American Airlines Logo
6:54 pm - 11:30 am
PWM
-
GCM
17h 36m
2 stops
American Airlines Logo
12:33 pm - 10:37 am
GCM
-
PWM
21h 04m
2 stops
$598American Airlines
Sun, Jun 14 - Wed, Jun 17
American Airlines Logo
11:57 am - 11:31 am
PWM
-
GCM
24h 34m
1 stop
American Airlines Logo
2:10 pm - 11:15 am
GCM
-
PWM
20h 05m
2 stops
$610American Airlines
Thu, Apr 30 - Thu, May 7
American Airlines Logo
5:57 pm - 11:30 am
PWM
-
GCM
18h 33m
1 stop
American Airlines Logo
12:33 pm - 10:47 pm
GCM
-
PWM
9h 14m
1 stop
$650American Airlines
Sun, Jun 14 - Wed, Jun 17

American Airlines flights from Portland, Maine to Cayman Islands

Our best American Airlines deals on Portland, Maine to Cayman Islands flight tickets
American Airlines
Sep 6
PWM6:50 pmPortland
19h 20m
2 stops
GCM1:10 pmGeorge Town Owen Roberts Intl
Sep 12
GCM1:20 pmGeorge Town Owen Roberts Intl
21h 11m
2 stops
PWM11:31 amPortland
$350
American Airlines
Apr 30
PWM6:01 pmPortland
18h 30m
2 stops
GCM11:31 amGeorge Town Owen Roberts Intl
May 7
GCM2:10 pmGeorge Town Owen Roberts Intl
20h 05m
2 stops
PWM11:15 amPortland
$450
American Airlines
Jun 10
PWM6:54 pmPortland
17h 07m
2 stops
GCM11:01 amGeorge Town Owen Roberts Intl
Jun 19
GCM5:12 pmGeorge Town Owen Roberts Intl
20h 12m
2 stops
PWM2:24 pmPortland
$455

United Airlines flights from Portland, Maine to Cayman Islands

Our best United Airlines deals on Portland, Maine to Cayman Islands flight tickets
United Airlines
May 22
PWM7:16 pmPortland
18h 19m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl
May 29
GCM1:35 pmGeorge Town Owen Roberts Intl
23h 51m
2 stops
PWM2:26 pmPortland
$819
United Airlines
May 22
PWM6:25 pmPortland
20h 05m
1 stop
GCM1:30 pmGeorge Town Owen Roberts Intl
May 29
GCM1:35 pmGeorge Town Owen Roberts Intl
19h 32m
2 stops
PWM10:07 amPortland
$832
United Airlines
Jun 14
PWM5:15 amPortland
32h 15m
3 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Jun 17
GCM1:35 pmGeorge Town Owen Roberts Intl
31h 16m
2 stops
PWM9:51 pmPortland
$967

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine to Cayman Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 10, 2026.
Use the filters below to find and compare flights from Portland, Maine to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 9/6

6:50 pm-1:10 pm

2 stops19h 20m

George Town Owen Roberts Intl

Sat 9/12

1:20 pm-11:31 am

2 stops21h 11m

$350

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 4/30

6:01 pm-11:31 am

2 stops18h 30m

George Town Owen Roberts Intl

Thu 5/7

2:10 pm-11:15 am

2 stops20h 05m

$450

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 6/10

6:54 pm-11:01 am

2 stops17h 07m

George Town Owen Roberts Intl

Fri 6/19

5:12 pm-2:24 pm

2 stops20h 12m

$455

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 9/6

11:57 am-11:25 am

1 stop24h 28m

George Town Owen Roberts Intl

Sat 9/12

1:20 pm-11:31 am

2 stops21h 11m

$461
Quickest round-trip

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 6/10

6:00 am-11:34 am

1 stop6h 34m

George Town Owen Roberts Intl

Fri 6/19

12:59 pm-11:15 pm

1 stop9h 16m

$493

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 6/14

5:57 pm-11:01 am

2 stops18h 04m

George Town Owen Roberts Intl

Wed 6/17

12:33 pm-10:47 pm

1 stop9h 14m

$550

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 6/10

5:57 pm-11:30 am

1 stop18h 33m

George Town Owen Roberts Intl

Fri 6/19

5:12 pm-2:24 pm

2 stops20h 12m

$566

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 6/14

6:54 pm-11:30 am

2 stops17h 36m

George Town Owen Roberts Intl

Wed 6/17

12:33 pm-10:37 am

2 stops21h 04m

$598

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 4/30

11:57 am-11:31 am

1 stop24h 34m

George Town Owen Roberts Intl

Thu 5/7

2:10 pm-11:15 am

2 stops20h 05m

$610

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 6/14

5:57 pm-11:30 am

1 stop18h 33m

George Town Owen Roberts Intl

Wed 6/17

12:33 pm-10:47 pm

1 stop9h 14m

$650

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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See travel insights to the Cayman Islands from

How to get the cheapest flight ticket from Portland, Maine to Cayman Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Portland to Cayman Islands?

American Airlines and United Airlines are the most popular carriers operating from Portland to Cayman Islands

What airlines fly to Cayman Islands?

American Airlines, JetBlue and United Airlines are the top three most popular airlines that fly to Cayman Islands from Portland, Maine according to our data. American Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Cayman Islands. Keep in mind that there are 4 different airlines that fly to Cayman Islands on a routine basis, so you have a few additional options to choose from.

Cheap Portland, Maine to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Cayman Islands

Fastest flight time

6h 34m

Direct flights

None
The fastest flight from Portland, Maine to Cayman Islands takes 6h 34m
There are no direct flights from Portland, Maine to Cayman Islands. There are no popular flight routes from Portland, Maine to Cayman Islands.
Search flight deals

Frequently asked questions about flying from Portland, Maine to the Cayman Islands

  • When did momondo last update prices for flights from Portland Airport to Cayman Islands?

    Prices for flights from Portland Airport to Cayman Islands refresh daily.

  • How many operators does momondo search for flights from Portland Airport to Cayman Islands?

  • How old do you have to be to fly from Portland Airport to Cayman Islands?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Cayman Islands.

  • What documentation or ID do you need to fly to Cayman Islands?

    The necessary travel and health documents for your Cayman Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Portland, Maine to Cayman Islands

Compare and see reviews for airlines that fly from Portland, Maine to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $200Free CancellationRating
7.4
9,562 reviews
Search United Airlines flights
DeltaPriceFrom $480Free CancellationRating
7.9
8,398 reviews
Search Delta flights
American AirlinesPriceFrom $504Free CancellationRating
7.1
11,564 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Cayman Islands?

Finding the right flight to Cayman Islands from Portland is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Cayman Islands quick and easy, saving you time and money.

Can I find flights from Portland to Cayman Islands with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Cayman Islands from Portland with this policy.

How can momondo help me find flights from Portland to Cayman Islands?

Once all potential Portland to Cayman Islands flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Portland to Cayman Islands right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Portland to Cayman Islands flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Cayman Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Find better results for your trip to the Cayman Islands

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