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Cheap flights from Portland, Maine to the Cayman Islands from $129

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 8/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
1:05 pm - 12:56 pm
PWM
-
GCM
23h 51m
1 stop
American Airlines Logo
3:45 pm - 12:11 pm
GCM
-
PWM
20h 26m
2 stops
$349American Airlines
Fri, Nov 27 - Fri, Dec 11
American Airlines Logo
6:39 pm - 12:40 pm
PWM
-
GCM
18h 01m
2 stops
American Airlines Logo
9:00 am - 10:33 pm
GCM
-
PWM
13h 33m
2 stops
$384American Airlines
Tue, Nov 17 - Tue, Dec 1
American Airlines Logo
6:39 pm - 12:40 pm
PWM
-
GCM
18h 01m
2 stops
American Airlines Logo
9:00 am - 10:33 pm
GCM
-
PWM
13h 33m
2 stops
$392American Airlines
Tue, Nov 17 - Tue, Dec 1
American Airlines Logo
6:46 pm - 1:10 pm
PWM
-
GCM
19h 24m
2 stops
American Airlines Logo
12:00 pm - 10:31 am
GCM
-
PWM
21h 31m
2 stops
$443American Airlines
Mon, Aug 10 - Mon, Aug 17
American Airlines Logo
6:40 pm - 12:15 pm
PWM
-
GCM
17h 35m
1 stop
American Airlines Logo
12:55 pm - 10:48 pm
GCM
-
PWM
9h 53m
1 stop
$445American Airlines
Tue, Dec 22 - Mon, Dec 28
American Airlines Logo
6:39 pm - 11:58 am
PWM
-
GCM
17h 19m
2 stops
American Airlines Logo
3:14 pm - 12:11 pm
GCM
-
PWM
20h 57m
2 stops
$460American Airlines
Fri, Nov 27 - Fri, Dec 11
American Airlines Logo
1:05 pm - 12:56 pm
PWM
-
GCM
23h 51m
1 stop
American Airlines Logo
3:14 pm - 10:34 pm
GCM
-
PWM
7h 20m
1 stop
$463American Airlines
Fri, Nov 27 - Fri, Dec 11
American Airlines Logo
7:17 am - 8:18 pm
PWM
-
GCM
13h 01m
2 stops
American Airlines Logo
3:11 pm - 10:48 pm
GCM
-
PWM
7h 37m
1 stop
$544American Airlines
Tue, Dec 22 - Mon, Dec 28
American Airlines Logo
7:24 pm - 11:27 am
PWM
-
GCM
17h 03m
1 stop
American Airlines Logo
4:00 pm - 11:38 am
GCM
-
PWM
18h 38m
2 stops
$560American Airlines
Sun, Aug 9 - Sat, Aug 15
American Airlines Logo
6:46 pm - 11:00 am
PWM
-
GCM
17h 14m
2 stops
American Airlines Logo
12:30 pm - 10:00 pm
GCM
-
PWM
8h 30m
1 stop
$561American Airlines
Mon, Aug 10 - Mon, Aug 17

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American Airlines flights from Portland, Maine to Cayman Islands

Our best American Airlines deals on Portland, Maine to Cayman Islands flight tickets
American Airlines
Nov 27
PWM1:05 pmPortland
23h 51m
1 stop
GCM12:56 pmGeorge Town Owen Roberts Intl
Dec 11
GCM3:45 pmGeorge Town Owen Roberts Intl
20h 26m
2 stops
PWM12:11 pmPortland
$349
American Airlines
Nov 17
PWM6:39 pmPortland
18h 01m
2 stops
GCM12:40 pmGeorge Town Owen Roberts Intl
Dec 1
GCM9:00 amGeorge Town Owen Roberts Intl
13h 33m
2 stops
PWM10:33 pmPortland
$384
American Airlines
Nov 17
PWM6:39 pmPortland
18h 01m
2 stops
GCM12:40 pmGeorge Town Owen Roberts Intl
Dec 1
GCM9:00 amGeorge Town Owen Roberts Intl
13h 33m
2 stops
PWM10:33 pmPortland
$392

United Airlines flights from Portland, Maine to Cayman Islands

Our best United Airlines deals on Portland, Maine to Cayman Islands flight tickets
United Airlines
Aug 9
PWM5:15 amPortland
32h 15m
3 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Aug 15
GCM2:45 pmGeorge Town Owen Roberts Intl
22h 49m
2 stops
PWM2:34 pmPortland
$871
United Airlines
Dec 28
PWM4:48 pmPortland
20h 27m
2 stops
GCM1:15 pmGeorge Town Owen Roberts Intl
Jan 4
GCM5:45 pmGeorge Town Owen Roberts Intl
27h 42m
2 stops
PWM9:27 pmPortland
$1,017
United Airlines
Dec 28
PWM4:48 pmPortland
23h 12m
2 stops
GCM4:00 pmGeorge Town Owen Roberts Intl
Jan 4
GCM5:10 pmGeorge Town Owen Roberts Intl
29h 47m
3 stops
PWM10:57 pmPortland
$1,056

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 July 14, 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

Fri 11/27

1:05 pm-12:56 pm

1 stop23h 51m

George Town Owen Roberts Intl

Fri 12/11

3:45 pm-12:11 pm

2 stops20h 26m

$349

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 11/17

6:39 pm-12:40 pm

2 stops18h 01m

George Town Owen Roberts Intl

Tue 12/1

9:00 am-10:33 pm

2 stops13h 33m

$384

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 11/17

6:39 pm-12:40 pm

2 stops18h 01m

George Town Owen Roberts Intl

Tue 12/1

9:00 am-10:33 pm

2 stops13h 33m

$392

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Mon 8/10

6:46 pm-1:10 pm

2 stops19h 24m

George Town Owen Roberts Intl

Mon 8/17

12:00 pm-10:31 am

2 stops21h 31m

$443

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 12/22

6:40 pm-12:15 pm

1 stop17h 35m

George Town Owen Roberts Intl

Mon 12/28

12:55 pm-10:48 pm

1 stop9h 53m

$445

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Fri 11/27

6:39 pm-11:58 am

2 stops17h 19m

George Town Owen Roberts Intl

Fri 12/11

3:14 pm-12:11 pm

2 stops20h 57m

$460

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Fri 11/27

1:05 pm-12:56 pm

1 stop23h 51m

George Town Owen Roberts Intl

Fri 12/11

3:14 pm-10:34 pm

1 stop7h 20m

$463
Quickest round-trip

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 12/22

7:17 am-8:18 pm

2 stops13h 01m

George Town Owen Roberts Intl

Mon 12/28

3:11 pm-10:48 pm

1 stop7h 37m

$544

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 8/9

7:24 pm-11:27 am

1 stop17h 03m

George Town Owen Roberts Intl

Sat 8/15

4:00 pm-11:38 am

2 stops18h 38m

$560

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Mon 8/10

6:46 pm-11:00 am

2 stops17h 14m

George Town Owen Roberts Intl

Mon 8/17

12:30 pm-10:00 pm

1 stop8h 30m

$561

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 month to fly to Cayman Islands?

If you aren’t able to travel to Cayman Islands during the month of September, then flying in July is also cheap. Prices for this month can be found on momondo for an average of $0.

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
9,988 reviews
Search United Airlines flights
DeltaPriceFrom $223Free CancellationRating
7.8
8,465 reviews
Search Delta flights
American AirlinesPriceFrom $439Free CancellationRating
7.1
11,808 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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Thu 8/13
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Find better results for your trip to the Cayman Islands

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Popular flights according to clicks in the last 7 days on momondo
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