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Cheap flights from Portland, Maine to the Cayman Islands from $301

This is the cheapest round-trip 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 2/28. 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
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
6:28 pm - 2:46 pm
PWM
-
GCM
20h 18m2 stops
American Airlines Logo
3:45 pm - 10:24 am
GCM
-
PWM
18h 39m2 stops
$301American Airlines
Sat, Feb 28 - Sat, Mar 7
Delta Logo
5:31 am - 12:29 pm
PWM
-
GCM
6h 58m1 stop
Delta Logo
1:12 pm - 11:22 pm
GCM
-
PWM
9h 10m1 stop
$320Delta
Wed, Feb 25 - Tue, Mar 10
American Airlines Logo
7:00 am - 2:26 pm
PWM
-
GCM
7h 26m1 stop
American Airlines Logo
12:35 pm - 10:54 pm
GCM
-
PWM
10h 19m1 stop
$321American Airlines
Sat, Jan 17 - Sat, Jan 24
Delta Logo
5:31 am - 12:29 pm
PWM
-
GCM
6h 58m1 stop
Delta Logo
1:54 pm - 12:18 am
GCM
-
PWM
10h 24m2 stops
$325Delta
Wed, Feb 25 - Thu, Mar 5
American Airlines Logo
3:58 pm - 11:50 am
PWM
-
GCM
19h 52m2 stops
American Airlines Logo
12:50 pm - 12:06 pm
GCM
-
PWM
23h 16m2 stops
$326American Airlines
Sat, Jan 17 - Sat, Jan 24
United Airlines Logo
6:00 am - 1:15 pm
PWM
-
GCM
7h 15m1 stop
United Airlines Logo
1:25 pm - 10:51 pm
GCM
-
PWM
8h 26m1 stop
$406United Airlines
Fri, Feb 27 - Tue, Mar 10
United Airlines Logo
3:05 pm - 1:45 pm
PWM
-
GCM
22h 40m2 stops
United Airlines Logo
2:25 pm - 11:20 pm
GCM
-
PWM
8h 55m1 stop
$411United Airlines
Wed, Feb 25 - Wed, Mar 4
United Airlines Logo
6:00 am - 1:15 pm
PWM
-
GCM
7h 15m1 stop
United Airlines Logo
1:50 pm - 3:14 pm
GCM
-
PWM
24h 24m1 stop
$414United Airlines
Fri, Feb 27 - Mon, Mar 9
American Airlines Logo
6:28 pm - 3:25 pm
PWM
-
GCM
20h 57m2 stops
American Airlines Logo
12:37 pm - 11:17 pm
GCM
-
PWM
10h 40m1 stop
$420American Airlines
Sat, Feb 28 - Sat, Mar 7
United Airlines Logo
6:00 am - 1:45 pm
PWM
-
GCM
31h 45m2 stops
United Airlines Logo
2:25 pm - 11:20 pm
GCM
-
PWM
8h 55m1 stop
$424United Airlines
Sat, Feb 28 - Wed, Mar 4

American Airlines flights from Portland, Maine to Cayman Islands

Our best American Airlines deals on Portland, Maine to Cayman Islands flight tickets
American Airlines
Feb 28
PWM6:28 pmPortland
20h 18m
2 stops
GCM2:46 pmGeorge Town Owen Roberts Intl
Mar 7
GCM3:45 pmGeorge Town Owen Roberts Intl
18h 39m
2 stops
PWM10:24 amPortland
$301
Find similar
American Airlines
Jan 17
PWM7:00 amPortland
7h 26m
1 stop
GCM2:26 pmGeorge Town Owen Roberts Intl
Jan 24
GCM12:35 pmGeorge Town Owen Roberts Intl
10h 19m
1 stop
PWM10:54 pmPortland
$321
Find similar
American Airlines
Jan 17
PWM3:58 pmPortland
19h 28m
2 stops
GCM11:26 amGeorge Town Owen Roberts Intl
Jan 24
GCM12:35 pmGeorge Town Owen Roberts Intl
10h 19m
1 stop
PWM10:54 pmPortland
$326
Find similar

United Airlines flights from Portland, Maine to Cayman Islands

Our best United Airlines deals on Portland, Maine to Cayman Islands flight tickets
United Airlines
Feb 27
PWM6:00 amPortland
7h 15m
1 stop
GCM1:15 pmGeorge Town Owen Roberts Intl
Mar 10
GCM1:25 pmGeorge Town Owen Roberts Intl
8h 26m
1 stop
PWM10:51 pmPortland
$406
Find similar
United Airlines
Feb 25
PWM3:05 pmPortland
22h 40m
2 stops
GCM1:45 pmGeorge Town Owen Roberts Intl
Mar 4
GCM2:25 pmGeorge Town Owen Roberts Intl
8h 55m
1 stop
PWM11:20 pmPortland
$411
Find similar
United Airlines
Feb 27
PWM6:00 amPortland
7h 15m
1 stop
GCM1:15 pmGeorge Town Owen Roberts Intl
Mar 9
GCM1:50 pmGeorge Town Owen Roberts Intl
24h 24m
1 stop
PWM3:14 pmPortland
$414
Find similar

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 December 27, 2025.
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

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 2/28

6:28 pm-2:46 pm

2 stops20h 18m

George Town Owen Roberts Intl

Sat 3/7

3:45 pm-10:24 am

2 stops18h 39m

$301

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 2/25

5:31 am-12:29 pm

1 stop6h 58m

George Town Owen Roberts Intl

Tue 3/10

1:12 pm-11:22 pm

1 stop9h 10m

$320

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 1/17

7:00 am-2:26 pm

1 stop7h 26m

George Town Owen Roberts Intl

Sat 1/24

12:35 pm-10:54 pm

1 stop10h 19m

$321

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 2/25

5:31 am-12:29 pm

1 stop6h 58m

George Town Owen Roberts Intl

Thu 3/5

1:54 pm-12:18 am

2 stops10h 24m

$325

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 1/17

3:58 pm-11:50 am

2 stops19h 52m

George Town Owen Roberts Intl

Sat 1/24

12:50 pm-12:06 pm

2 stops23h 16m

$326

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Fri 2/27

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Tue 3/10

1:25 pm-10:51 pm

1 stop8h 26m

$406

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 2/25

3:05 pm-1:45 pm

2 stops22h 40m

George Town Owen Roberts Intl

Wed 3/4

2:25 pm-11:20 pm

1 stop8h 55m

$411

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Fri 2/27

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Mon 3/9

1:50 pm-3:14 pm

1 stop24h 24m

$414

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 2/28

6:28 pm-3:25 pm

2 stops20h 57m

George Town Owen Roberts Intl

Sat 3/7

12:37 pm-11:17 pm

1 stop10h 40m

$420

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 2/28

6:00 am-1:45 pm

2 stops31h 45m

George Town Owen Roberts Intl

Wed 3/4

2:25 pm-11:20 pm

1 stop8h 55m

$424

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 day to depart on your flight to Cayman Islands?

Our data shows that Tuesday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $469. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Saturday is $1,028.

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

7h 15m

Direct flights

None
The fastest flight from Portland, Maine to Cayman Islands takes 7h 15m
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

  • 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 $293Free CancellationRating
7.4
9,116 reviews
Search United Airlines flights
DeltaPriceFrom $504Free CancellationRating
7.9
8,018 reviews
Search Delta flights
American AirlinesPriceFrom $510Free CancellationRating
7.2
11,067 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

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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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