What are the most popular airlines that fly from Portland, Maine to Cayman Islands?

Before booking your flight from Portland, Maine to Cayman Islands check out the most popular airlines for this route: American Airlines, Delta or United Airlines.

What is the cheapest month to fly from Portland, Maine to Cayman Islands?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, January can be a great choice for travel to Cayman Islands. Flights to Cayman Islands from Portland, Maine in January are about $702 on average during January, but can be found for as low as $386.

What is the cheapest time of day to fly from PWM to KY?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Cayman Islands as you normally would.

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.

$620+ Flights from Portland, ME to the Cayman Islands

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Cheap flight deals from Portland to Cayman Islands

Most accurate provider	FlightHub 3 stars
Most trusted provider	Expedia 3 stars
Round-trip from	$542 (American Airlines)
Popular in	December
Cheapest in	January
Average price	$746

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. 25% potential increase in price ($235 potential increase over avg. RT price).

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Cheapest flight prices on average. 15% potential price decrease ($96 potential savings vs. average RT price).

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Average for round-trip flights in April 2025

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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 April 17, 2025.

Sat 12/64:16 pmPWM - GCM

2 stops19h 49mAmerican Airlines

Sat 12/134:15 pmGCM - PWM

2 stops19h 20mAmerican Airlines

Deal found 4/17

$542

Wed 7/306:00 amPWM - GCM

1 stop6h 31mDelta

Thu 8/1412:50 pmGCM - PWM

1 stop10h 09mDelta

Deal found 4/17

$548

Wed 7/307:15 pmPWM - GCM

2 stops18h 15mUnited Airlines

Sun 8/171:35 pmGCM - PWM

2 stops23h 49mUnited Airlines

Deal found 4/17

$566

Wed 8/136:00 amPWM - GCM

2 stops30h 55mAir Canada

Mon 8/2512:50 pmGCM - PWM

2 stops23h 59mAir Canada

Deal found 4/17

$823

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 April 17, 2025.

Fri 8/16:01 pmPWM - GCM

2 stops21h 14mAmerican Airlines

Fri 8/153:20 pmGCM - PWM

2 stops19h 40mAmerican Airlines

Deal found 4/17

$542

Wed 7/306:00 amPWM - GCM

1 stop6h 31mDelta

Fri 8/1512:50 pmGCM - PWM

1 stop10h 09mDelta

Deal found 4/17

$548

Wed 7/307:15 pmPWM - GCM

2 stops18h 15mUnited Airlines

Sun 8/171:35 pmGCM - PWM

2 stops23h 49mUnited Airlines

Deal found 4/17

$566

Wed 8/136:00 amPWM - GCM

2 stops30h 55mAir Canada

Mon 8/2512:50 pmGCM - PWM

2 stops23h 59mAir Canada

Deal found 4/17

$823

Cheapflights Fare Finder

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

Fri 8/1

6:01 pm-2:15 pm

2 stops21h 14m

George Town Owen Roberts Intl

Fri 8/15

3:20 pm-12:00 pm

2 stops19h 40m

$542

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 7/30

6:00 am-11:31 am

1 stop6h 31m

George Town Owen Roberts Intl

Fri 8/15

12:50 pm-11:59 pm

1 stop10h 09m

$548

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 7/30

7:15 pm-12:30 pm

2 stops18h 15m

George Town Owen Roberts Intl

Sun 8/17

1:35 pm-2:24 pm

2 stops23h 49m

$566

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 8/13

6:00 am-11:55 am

2 stops30h 55m

George Town Owen Roberts Intl

Mon 8/25

12:50 pm-1:49 pm

2 stops23h 59m

$823

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

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

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta

8.0

Very good

7,917 reviews

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines

7.4

Good

8,667 reviews

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air Canada

7.0

Good

9,142 reviews

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

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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Alternative routes for Portland to Cayman Islands

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Augusta to Luis Munoz Marin Intl flights

Top 3 airlines flying from Portland to Cayman Islands

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$386	Average$467	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$467	Average$617	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$521	Average$694	FlexibilityNo cancel fee	On-time71%

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$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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Portland to Cayman Islands with Cheapflights

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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 April 17, 2025.

Most accurate provider

Most trusted provider

Round-trip from

Popular in

Cheapest in

Average price

Find flight deals from Portland to Cayman Islands

Cheapest flights from Portland to Cayman IslandsExplore 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 April 17, 2025.

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 April 17, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Portland to the Cayman Islands that are best for you.

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.

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?

Reviews of airlines servicing Cayman Islands

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?

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

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

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Portland to Cayman Islands

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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 April 17, 2025.