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Cayman Islands

$315+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Find 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 October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/26. 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 12/115:17 pmPWM - GCM
2 stops20h 49mAmerican Airlines
Tue 12/161:25 pmGCM - PWM
2 stops10h 12mAmerican Airlines
Deal found 10/26$315
This Delta deal was found by Cheapflights users on 10/27. 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.
Thu 11/66:00 amPWM - GCM
1 stop6h 44mDelta
Mon 11/101:50 pmGCM - PWM
1 stop8h 29mDelta
Deal found 10/27$328
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 11/67:22 pmPWM - GCM
2 stops21h 08mUnited Airlines
Mon 11/105:45 pmGCM - PWM
2 stops19h 51mUnited Airlines
Deal found 10/27$443
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/215:20 pmPWM - GCM
2 stops21h 01mAmerican Airlines
Fri 1/23:45 pmGCM - PWM
2 stops20h 26mAmerican Airlines
Deal found 10/27$830

Cheap 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 October 28, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$315
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$545
Provider with most accurate pricing for Portland-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Portland-George Town Owen Roberts Intl flights.
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From Portland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 27% potential increase in price ($266 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($73 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 28, 2025.
Use the filters below to find and compare flights from Portland to the Cayman Islands that are best for you.

Fly from

Portland

Fly to

Cayman Islands

Route

Depart

Return

Price

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 2/5

3:56 pm-11:26 am

2 stops19h 30m

George Town Owen Roberts Intl

Tue 2/10

3:45 pm-12:05 pm

2 stops20h 20m

$327

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 2/5

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Tue 2/10

2:25 pm-2:31 pm

2 stops24h 06m

$327

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

$328

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 3/4

5:30 am-12:35 pm

1 stop7h 05m

George Town Owen Roberts Intl

Tue 3/10

1:00 pm-9:59 pm

1 stop7h 59m

$328

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

$429

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 12/11

6:00 am-2:24 pm

2 stops8h 24m

George Town Owen Roberts Intl

Tue 12/16

12:50 pm-9:37 pm

1 stop8h 47m

$437

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

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, November is the cheapest month in which you can book a flight from Portland, Maine to Cayman Islands (average of $235). Flying from Portland, Maine to Cayman Islands in June is currently the most expensive (average of $419). 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 October 28, 2025.
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
7,994 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 American Airlines, United Airlines, and Delta fly from Portland, Maine to Cayman Islands in about 7h 05m. The time it takes to get you to your destination can typically vary by up to 12h 25m. 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, November is the cheapest month in which you can book a flight from Portland, Maine to Cayman Islands (average of $235). Flying from Portland, Maine to Cayman Islands in June is currently the most expensive (average of $419). 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

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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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$504Average$622FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$506Average$586FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$536Average$681FlexibilityNo cancel feeOn-time69%

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