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Cayman Islands

$299+ Cheap flights from Portland, ME (PWM) to the Cayman Islands

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Mar 28 — Apr 41
Sat 3/28
Sat 4/4
1 adult, Economy
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Cheap flight deals from Portland to Cayman Islands

Cheapest flights from Portland to Cayman Islands
Explore the most affordable flight options available from Portland to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 26, 2026.

This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:01 pm
PWM
-
GCM
2 stops18h 30m
American Airlines
Wed 4/152:05 pm
GCM
-
PWM
2 stops20h 10m
American Airlines
Deal found 2/25$299
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/225:40 pm
PWM
-
GCM
2 stops18h 30m
American Airlines
Wed 3/257:45 am
GCM
-
PWM
2 stops14h 05m
American Airlines
Deal found 2/23$312
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:29 pm
PWM
-
GCM
2 stops17h 36m
American Airlines
Tue 3/312:44 pm
GCM
-
PWM
1 stop25h 23m
American Airlines
Deal found 2/25$319
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:31 am
PWM
-
GCM
1 stop6h 58m
Delta
Mon 3/91:12 pm
GCM
-
PWM
1 stop9h 10m
Delta
Deal found 2/25$339
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:59 pm
PWM
-
GCM
2 stops18h 30m
Delta
Tue 3/101:12 pm
GCM
-
PWM
2 stops23h 38m
Delta
Deal found 2/25$344
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:23 pm
PWM
-
GCM
2 stops17h 08m
American Airlines
Thu 4/1612:35 pm
GCM
-
PWM
2 stops20h 32m
American Airlines
Deal found 2/25$346
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:40 pm
PWM
-
GCM
1 stop20h 55m
American Airlines
Mon 3/212:58 pm
GCM
-
PWM
1 stop9h 52m
American Airlines
Deal found 2/25$347
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/910:50 am
PWM
-
GCM
2 stops27h 20m
American Airlines
Tue 4/1412:00 pm
GCM
-
PWM
2 stops25h 37m
American Airlines
Deal found 2/25$359
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:23 pm
PWM
-
GCM
2 stops18h 47m
American Airlines
Thu 5/712:00 pm
GCM
-
PWM
2 stops34h 27m
American Airlines
Deal found 2/25$361
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:00 am
PWM
-
GCM
1 stop7h 15m
United Airlines
Tue 3/101:25 pm
GCM
-
PWM
1 stop8h 39m
United Airlines
Deal found 2/23$364
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:57 am
PWM
-
GCM
1 stop24h 34m
American Airlines
Tue 5/52:10 pm
GCM
-
PWM
2 stops18h 44m
American Airlines
Deal found 2/25$367

Find flight deals from Portland to Cayman Islands

Keep the following information in mind while searching for Portland to Cayman Islands flight deals. Data was last updated February 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$299
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$598
Provider with most accurate pricing for Boston Logan Intl-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-George Town Owen Roberts Intl flights.
Search Deals
From Portland to Cayman Islands
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland 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, Cheapflights users made 2,558,603 searches. Data last updated February 26, 2026.
Use the filters below to find and compare flights from Portland to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 3/15

6:00 am-12:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Thu 3/19

1:25 pm-10:51 pm

1 stop8h 26m

$380

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 4/11

6:00 am-1:20 pm

1 stop8h 20m

George Town Owen Roberts Intl

Sat 4/18

2:10 pm-11:59 pm

1 stop8h 49m

$455

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 4/8

6:04 am-12:45 pm

1 stop7h 41m

George Town Owen Roberts Intl

Wed 4/15

1:50 pm-2:20 pm

1 stop23h 30m

$479

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 4/21

6:04 am-12:45 pm

1 stop7h 41m

George Town Owen Roberts Intl

Mon 4/27

1:50 pm-2:20 pm

1 stop23h 30m

$542

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 4/9

7:36 pm-12:00 pm

2 stops17h 24m

George Town Owen Roberts Intl

Thu 4/16

1:50 pm-9:40 pm

1 stop30h 50m

$559

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 6/14

5:36 pm-11:02 am

2 stops18h 26m

George Town Owen Roberts Intl

Wed 6/17

5:11 pm-2:24 pm

2 stops20h 13m

$564

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 5/9

5:30 am-3:05 pm

1 stop10h 35m

George Town Owen Roberts Intl

Wed 5/13

1:35 pm-11:59 pm

2 stops33h 24m

$569

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/25

Sorted by cheapest first

Best time to book a flight from Portland to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Portland 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.

Cheapflights Insights

Everything you need to know about your flight from Portland to the Cayman Islands

What is the cheapest month to book a flight from Portland, Maine to Cayman Islands?

Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Cayman Islands (average of $72). Flying from Portland, Maine to Cayman Islands in August is currently the most expensive (average of $404). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cayman Islands. Reviews last updated February 26, 2026.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Portland to the Cayman Islands have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,237 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Comfort

7.9

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,237 reviews
Delta
7.9
Good
8,237 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Comfort

7.9

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,348 reviews
Delta
7.9
Good
8,237 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Comfort

7.9

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,352 reviews
Delta
7.9
Good
8,237 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Comfort

7.9

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Portland to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Portland to Cayman Islands?

    Located just 2.9 mi from the city center, Portland (PWM) is the airport most travelers will use when flying to Cayman Islands from Portland.

  • How long is the flight from Portland, Maine to Cayman Islands?

    Airlines like United Airlines and JetBlue fly from Portland, Maine to Cayman Islands in about 7h 15m. The time it takes to get you to your destination can typically vary by up to 1h 05m. There are 1799 mi between Portland, Maine and Cayman Islands. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Portland to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Portland to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Cayman Islands.

  • Can I find deals for business class flights from Portland to Cayman Islands?

    Yes. Cheapflights offers flight deals from Portland to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland, Maine to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Cayman Islands (average of $72). Flying from Portland, Maine to Cayman Islands in August is currently the most expensive (average of $404). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Portland to Cayman Islands

Discover the top 3 airlines that operate flights from Portland to Cayman Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$200Average$478FlexibilityNo cancel feeOn-time69%
DeltaCheapest$480Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$506Average$587FlexibilityNo cancel feeOn-time71%

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