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Cayman Islands

$317+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Jan 28 — Feb 41
Wed 1/28
Wed 2/4
1 adult, Economy
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Cheap flight deals from Portland to Cayman Islands

Best flights from Portland to Cayman Islands
Discover carefully curated flight deals from Portland to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 29, 2025.

This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:31 amPWM - GCM
1 stop6h 58mDelta
Tue 3/101:12 pmGCM - PWM
1 stop9h 10mDelta
Deal found 12/26$320
This American Airlines deal was found by Cheapflights users on 12/29. 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 1/275:20 amPWM - GCM
2 stops15h 00mAmerican Airlines
Sun 2/13:45 pmGCM - PWM
2 stops20h 20mAmerican Airlines
Deal found 12/29$320
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:31 amPWM - GCM
1 stop6h 58mDelta
Mon 3/91:12 pmGCM - PWM
1 stop9h 10mDelta
Deal found 12/26$320
This American Airlines deal was found by Cheapflights users on 12/27. 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.
Sat 1/175:09 pmPWM - GCM
2 stops18h 17mAmerican Airlines
Sat 1/2412:35 pmGCM - PWM
1 stop10h 19mAmerican Airlines
Deal found 12/27$326
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:31 amPWM - GCM
1 stop6h 58mDelta
Mon 3/91:12 pmGCM - PWM
2 stops9h 47mDelta
Deal found 12/26$325
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/312:13 pmPWM - GCM
2 stops24h 16mDelta
Thu 3/51:54 pmGCM - PWM
2 stops10h 24mDelta
Deal found 12/26$325
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/252:35 pmPWM - GCM
2 stops21h 54mDelta
Mon 3/91:12 pmGCM - PWM
2 stops20h 52mDelta
Deal found 12/26$325
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2512:43 pmPWM - GCM
2 stops23h 46mDelta
Thu 3/51:54 pmGCM - PWM
2 stops10h 24mDelta
Deal found 12/26$325
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:31 amPWM - GCM
1 stop6h 58mDelta
Thu 3/51:54 pmGCM - PWM
2 stops10h 24mDelta
Deal found 12/26$325

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 December 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$301
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$1,281
Provider with most accurate pricing for Portland-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-George Town Owen Roberts Intl flights.
Search Deals
From Portland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($213 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($61 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 29, 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 2/26

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

Tue 1/27

5:20 am-8:20 pm

2 stops15h 00m

George Town Owen Roberts Intl

Sun 2/1

3:45 pm-12:05 pm

2 stops20h 20m

$320

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 2/26

5:31 am-12:29 pm

1 stop6h 58m

George Town Owen Roberts Intl

Mon 3/9

1:12 pm-11:22 pm

1 stop9h 10m

$320

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 3/3

5:31 am-12:29 pm

1 stop6h 58m

George Town Owen Roberts Intl

Mon 3/9

1:12 pm-11:59 pm

2 stops9h 47m

$325

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 3/3

12:13 pm-12:29 pm

2 stops24h 16m

George Town Owen Roberts Intl

Thu 3/5

1:54 pm-12:18 am

2 stops10h 24m

$325

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 2/25

2:35 pm-12:29 pm

2 stops21h 54m

George Town Owen Roberts Intl

Mon 3/9

1:12 pm-11:04 am

2 stops20h 52m

$325

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 2/25

12:43 pm-12:29 pm

2 stops23h 46m

George Town Owen Roberts Intl

Thu 3/5

1:54 pm-12:18 am

2 stops10h 24m

$325

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 2/26

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

5:09 pm-11:26 am

2 stops18h 17m

George Town Owen Roberts Intl

Sat 1/24

12:35 pm-10:54 pm

1 stop10h 19m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

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, January is the cheapest month in which you can book a flight from Portland, Maine to Cayman Islands (average of $195). 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 December 29, 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
8,014 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

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
8,014 reviews
Delta
7.9
Good
8,014 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

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
9,118 reviews
Delta
7.9
Good
8,014 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

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
11,072 reviews
Delta
7.9
Good
8,014 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

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 Delta and American Airlines fly from Portland, Maine to Cayman Islands in about 6h 58m. The time it takes to get you to your destination can typically vary by up to 8h 02m. 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 $195). 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 December 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$200Average$617FlexibilityNo cancel feeOn-time69%
DeltaCheapest$480Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$510Average$587FlexibilityNo cancel feeOn-time71%

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