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Cayman Islands

$542+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$642
(American Airlines)
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
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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 March 28, 2025.

This American Airlines deal was found by Cheapflights users on 3/27. 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 12/65:53 amPWM - GCM
1 stop6h 22mAmerican Airlines
Sat 12/132:15 pmGCM - PWM
2 stops21h 41mAmerican Airlines
Deal found 3/27$542
This United deal was found by Cheapflights users on 3/28. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/156:10 amPWM - GCM
3 stops31h 20mUnited Airlines
Sat 6/211:45 pmGCM - PWM
2 stops24h 08mUnited Airlines
Deal found 3/28$830

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 March 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

Sun 6/15

6:01 pm-1:10 pm

2 stops20h 09m

George Town Owen Roberts Intl

Sat 6/21

12:25 pm-11:01 pm

1 stop9h 36m

$642

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 6/15

6:10 am-12:30 pm

3 stops31h 20m

George Town Owen Roberts Intl

Sat 6/21

1:45 pm-2:53 pm

2 stops24h 08m

$830

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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 March 28, 2025.
United Airlines
7.4
Good
8,603 reviews

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.0

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,603 reviews
United Airlines
7.4
Good
8,603 reviews

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.0

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,603 reviews

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.0

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$386Average$504FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$467Average$617FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$521Average$704FlexibilityNo cancel feeOn-time71%
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