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Grand Cayman

$235+ Cheap flights from Portland, ME (PWM) to Grand Cayman

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Portland to Grand Cayman

Cheapest flights from Portland to Grand Cayman
Explore the most affordable flight options available from Portland to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Delta deal was found by Cheapflights users on 12/16. 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 12/235:45 amPWM - GCM
1 stop6h 51mDelta
Fri 12/263:42 pmGCM - PWM
1 stop7h 01mDelta
Deal found 12/16$328
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Tue 12/237:30 pmPWM - GCM
2 stops18h 15mUnited Airlines
Fri 12/262:25 pmGCM - PWM
1 stop8h 57mUnited Airlines
Deal found 12/16$456
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Sun 12/217:30 pmPWM - GCM
2 stops18h 15mUnited Airlines
Fri 1/25:45 pmGCM - PWM
2 stops27h 44mUnited Airlines
Deal found 12/16$689
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/215:39 amPWM - GCM
2 stops8h 42mAmerican Airlines
Fri 1/27:30 amGCM - PWM
2 stops16h 15mAmerican Airlines
Deal found 12/17$707
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/317:30 pmPWM - GCM
2 stops20h 30mUnited Airlines
Fri 1/25:45 pmGCM - PWM
2 stops19h 54mUnited Airlines
Deal found 12/17$864
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/305:45 amPWM - GCM
2 stops8h 36mAmerican Airlines
Sun 1/47:30 amGCM - PWM
2 stops16h 15mAmerican Airlines
Deal found 12/16$899
This Delta deal was found by Cheapflights users on 12/17. 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 12/215:45 amPWM - GCM
1 stop8h 42mDelta
Fri 1/23:42 pmGCM - PWM
1 stop7h 01mDelta
Deal found 12/17$907

Find flight deals from Portland to Grand Cayman

Keep the following information in mind while searching for Portland to Grand Cayman flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$296
(United Airlines)

One-way from

$235
(United Airlines)

Popular in

December

Cheapest in

March

Average price

$644
Provider with most accurate pricing for Boston Logan Intl-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-George Town Owen Roberts Intl flights.
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From Portland to Grand Cayman
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One-way flight from Portland to Grand Cayman
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Grand Cayman 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 18, 2025.
Use the filters below to find and compare flights from Portland to Grand Cayman that are best for you.

Fly from

Portland

Fly to

Grand Cayman

Route

Depart

Return

Price

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

$306

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Mon 1/5

6:41 pm-2:45 pm

2 stops20h 04m

George Town Owen Roberts Intl

Sat 1/10

3:24 pm-12:05 pm

2 stops20h 41m

$317

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 1/7

5:30 am-12:40 pm

1 stop7h 10m

George Town Owen Roberts Intl

Mon 1/12

2:05 pm-10:27 pm

1 stop8h 22m

$320

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 1/7

5:30 am-12:40 pm

1 stop7h 10m

George Town Owen Roberts Intl

Sat 1/10

3:25 pm-10:27 pm

1 stop7h 02m

$320

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Fri 2/27

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Wed 3/4

2:25 pm-11:20 pm

1 stop8h 55m

$323

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 1/8

12:20 pm-12:40 pm

2 stops24h 20m

George Town Owen Roberts Intl

Mon 1/12

2:05 pm-10:27 pm

1 stop8h 22m

$325

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 1/11

5:30 am-12:40 pm

1 stop7h 10m

George Town Owen Roberts Intl

Mon 1/12

2:05 pm-12:20 am

2 stops10h 15m

$325

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 1/10

6:17 am-12:40 pm

2 stops30h 23m

George Town Owen Roberts Intl

Mon 1/12

2:05 pm-10:27 pm

1 stop8h 22m

$325

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 1/6

2:30 pm-12:40 pm

2 stops22h 10m

George Town Owen Roberts Intl

Mon 1/12

2:05 pm-10:27 pm

1 stop8h 22m

$325

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 1/6

2:30 pm-12:40 pm

2 stops22h 10m

George Town Owen Roberts Intl

Sat 1/10

12:25 pm-11:20 am

2 stops22h 55m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 14 results
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Best time to book a flight from Portland to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman 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 Grand Cayman

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

Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Grand Cayman (average of $194). Flying from Portland, Maine to Grand Cayman 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 Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated December 18, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Portland to Grand Cayman to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,005 reviews

Overall

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

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
8,005 reviews
Delta
7.9
Good
8,005 reviews

Overall

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

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
9,091 reviews
Delta
7.9
Good
8,005 reviews

Overall

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

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
11,054 reviews
Delta
7.9
Good
8,005 reviews

Overall

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

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 Grand Cayman. 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 Grand Cayman?

    Located just 2.9 mi from the city center, Portland (PWM) is the airport most travelers will use when flying to Grand Cayman from Portland.

  • How long is the flight from Portland, Maine to Grand Cayman?

    For as low as $320, American Airlines can have you in Grand Cayman from Portland, Maine in 7h 10m. The distance from Portland, Maine to Grand Cayman is about 1799 mi. This flight may include one or multiple stops.

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

    Yes. In addition to deals on Portland to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Grand Cayman?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Grand Cayman.

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

    Yes. Cheapflights offers flight deals from Portland to Grand Cayman 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 Grand Cayman?

    Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Grand Cayman (average of $194). Flying from Portland, Maine to Grand Cayman 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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Alternative routes for Portland to Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
Boston to George Town flights
Portland to George Town flights
Boston to Cayman Brac flights

Top 3 airlines flying from Portland to Grand Cayman

Discover the top 3 airlines that operate flights from Portland to Grand Cayman. 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$293Average$681FlexibilityNo cancel feeOn-time69%
DeltaCheapest$504Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$506Average$586FlexibilityNo cancel feeOn-time71%

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