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Cayman Islands

$455+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Jul 30 — Aug 61
Wed 7/30
Wed 8/6
1 adult, Economy
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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 July 25, 2025.

Round-trip from

$455
(Delta)

Popular in

December

Cheapest in

January

Average price

$526
From Portland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($170 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 July 2025
Search Deals

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 July 25, 2025.

This Delta deal was found by Cheapflights users on 7/24. 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.
Sun 9/146:00 amPWM - GCM
1 stop6h 36mDelta
Sat 9/2012:52 pmGCM - PWM
1 stop8h 08mDelta
Deal found 7/24$455
This American Airlines deal was found by Cheapflights users on 7/24. 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 9/146:05 pmPWM - GCM
2 stops18h 05mAmerican Airlines
Sat 9/2012:10 pmGCM - PWM
2 stops23h 19mAmerican Airlines
Deal found 7/24$523

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 July 25, 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

Sun 9/14

6:00 am-11:36 am

1 stop6h 36m

George Town Owen Roberts Intl

Sat 9/20

12:52 pm-10:00 pm

1 stop8h 08m

$455

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 9/14

6:05 pm-11:10 am

2 stops18h 05m

George Town Owen Roberts Intl

Sat 9/20

12:10 pm-12:29 pm

2 stops23h 19m

$523

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

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 $467). Flying from Portland, Maine to Cayman Islands in March is currently the most expensive (average of $594). 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 July 25, 2025.
See what other customers who have flown with Delta 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
8.0
Very good
7,967 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,967 reviews
Delta
8.0
Very good
7,967 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,967 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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 $467). Flying from Portland, Maine to Cayman Islands in March is currently the most expensive (average of $594). 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 July 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$386Average$560FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$469Average$617FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$510Average$640FlexibilityNo cancel feeOn-time71%

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