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Cheap flights from Portland, Maine to the Cayman Islands from $556

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 3/10. 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.
Delta Logo
5:30 am - 11:35 amPWM-GCM
7h 05m1 stop
Delta Logo
1:00 pm - 9:59 pmGCM-PWM
7h 59m1 stop
$556Delta
Find Deal
Tue, Mar 10 - Wed, Mar 11
American Airlines Logo
6:37 pm - 2:46 pmPWM-GCM
20h 09m2 stops
American Airlines Logo
12:55 pm - 9:35 pmGCM-PWM
8h 40m1 stop
$561American Airlines
Find Deal
Thu, Nov 6 - Mon, Nov 10
American Airlines Logo
3:56 pm - 12:05 pmPWM-GCM
20h 09m2 stops
American Airlines Logo
12:50 pm - 12:06 pmGCM-PWM
23h 16m2 stops
$566American Airlines
Find Deal
Tue, Jan 27 - Sun, Feb 1
American Airlines Logo
7:02 am - 2:14 pmPWM-GCM
7h 12m1 stop
American Airlines Logo
12:55 pm - 9:35 pmGCM-PWM
8h 40m1 stop
$600American Airlines
Find Deal
Thu, Nov 6 - Mon, Nov 10
American Airlines Logo
7:02 am - 2:14 pmPWM-GCM
7h 12m1 stop
American Airlines Logo
12:55 pm - 11:59 pmGCM-PWM
11h 04m2 stops
$605American Airlines
Find Deal
Thu, Nov 6 - Mon, Nov 10
American Airlines Logo
7:50 am - 1:20 pmPWM-GCM
6h 30m1 stop
American Airlines Logo
3:15 pm - 11:34 amGCM-PWM
19h 19m2 stops
$610American Airlines
Find Deal
Mon, Apr 6 - Sun, Apr 12
Delta Logo
6:00 am - 12:44 pmPWM-GCM
6h 44m1 stop
Delta Logo
1:50 pm - 10:19 pmGCM-PWM
8h 29m1 stop
$640Delta
Find Deal
Thu, Nov 6 - Mon, Nov 10
United Airlines Logo
2:14 pm - 4:35 pmPWM-GCM
26h 21m1 stop
United Airlines Logo
5:10 pm - 11:59 pmGCM-PWM
6h 49m1 stop
$676United Airlines
Find Deal
Sun, Dec 21 - Fri, Jan 2
United Airlines Logo
6:00 am - 1:15 pmPWM-GCM
7h 15m1 stop
United Airlines Logo
2:50 pm - 2:39 pmGCM-PWM
23h 49m1 stop
$678United Airlines
Find Deal
Tue, Jan 27 - Sun, Feb 1
United Airlines Logo
6:00 am - 4:35 pmPWM-GCM
10h 35m2 stops
United Airlines Logo
5:10 pm - 6:27 pmGCM-PWM
25h 17m2 stops
$686United Airlines
Find Deal
Sun, Dec 21 - Fri, Jan 2

Delta flights from Portland, Maine to Cayman Islands

Our best Delta deals on Portland, Maine to Cayman Islands flight tickets
Delta
Mar 10
PWM5:30 amPortland
7h 05m
1 stop
GCM11:35 amGeorge Town Owen Roberts Intl
Mar 11
GCM1:00 pmGeorge Town Owen Roberts Intl
7h 59m
1 stop
PWM9:59 pmPortland
$556
Find similar
Delta
Nov 6
PWM6:00 amPortland
6h 44m
1 stop
GCM12:44 pmGeorge Town Owen Roberts Intl
Nov 10
GCM1:50 pmGeorge Town Owen Roberts Intl
8h 29m
1 stop
PWM10:19 pmPortland
$640
Find similar
Delta
Dec 28
PWM5:36 amPortland
8h 51m
1 stop
GCM2:27 pmGeorge Town Owen Roberts Intl
Jan 1
GCM3:42 pmGeorge Town Owen Roberts Intl
7h 01m
1 stop
PWM10:43 pmPortland
$931
Find similar

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 6
PWM6:37 pmPortland
20h 09m
2 stops
GCM2:46 pmGeorge Town Owen Roberts Intl
Nov 10
GCM12:55 pmGeorge Town Owen Roberts Intl
8h 40m
1 stop
PWM9:35 pmPortland
$561
Find similar
American Airlines
Jan 27
PWM3:56 pmPortland
20h 09m
2 stops
GCM12:05 pmGeorge Town Owen Roberts Intl
Feb 1
GCM12:50 pmGeorge Town Owen Roberts Intl
23h 16m
2 stops
PWM12:06 pmPortland
$566
Find similar
American Airlines
Nov 6
PWM7:02 amPortland
7h 12m
1 stop
GCM2:14 pmGeorge Town Owen Roberts Intl
Nov 10
GCM12:55 pmGeorge Town Owen Roberts Intl
8h 40m
1 stop
PWM9:35 pmPortland
$600
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 October 13, 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

Tue 3/10

5:30 am-11:35 am

1 stop7h 05m

George Town Owen Roberts Intl

Wed 3/11

1:00 pm-9:59 pm

1 stop7h 59m

$556

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 11/6

6:37 pm-2:46 pm

2 stops20h 09m

George Town Owen Roberts Intl

Mon 11/10

12:55 pm-9:35 pm

1 stop8h 40m

$561

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 1/27

3:56 pm-12:05 pm

2 stops20h 09m

George Town Owen Roberts Intl

Sun 2/1

12:50 pm-12:06 pm

2 stops23h 16m

$566

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 11/6

7:02 am-2:14 pm

1 stop7h 12m

George Town Owen Roberts Intl

Mon 11/10

12:55 pm-9:35 pm

1 stop8h 40m

$600

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 11/6

7:02 am-2:14 pm

1 stop7h 12m

George Town Owen Roberts Intl

Mon 11/10

12:55 pm-11:59 pm

2 stops11h 04m

$605

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Mon 4/6

7:50 am-1:20 pm

1 stop6h 30m

George Town Owen Roberts Intl

Sun 4/12

3:15 pm-11:34 am

2 stops19h 19m

$610

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 11/6

6:00 am-12:44 pm

1 stop6h 44m

George Town Owen Roberts Intl

Mon 11/10

1:50 pm-10:19 pm

1 stop8h 29m

$640

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 12/21

2:14 pm-4:35 pm

1 stop26h 21m

George Town Owen Roberts Intl

Fri 1/2

5:10 pm-11:59 pm

1 stop6h 49m

$676

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 1/27

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sun 2/1

2:50 pm-2:39 pm

1 stop23h 49m

$678

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 12/21

6:00 am-4:35 pm

2 stops10h 35m

George Town Owen Roberts Intl

Fri 1/2

5:10 pm-6:27 pm

2 stops25h 17m

$686

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

Direct flights

None
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
DeltaPriceFrom $504Free CancellationRating
7.9
7,971 reviews
Search Delta flights
American AirlinesPriceFrom $506Free CancellationRating
7.2
11,046 reviews
Search American Airlines flights
United AirlinesPriceFrom $536Free CancellationRating
7.4
8,970 reviews
Search United 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.

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