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Grand Cayman

$320+ Cheap flights from Portland, ME (PWM) to Grand Cayman

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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Find 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 November 4, 2025.

This American Airlines deal was found by Cheapflights users on 11/4. 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.
Thu 11/65:37 pmPWM - GCM
2 stops18h 19mAmerican Airlines
Mon 11/101:20 pmGCM - PWM
2 stops22h 26mAmerican Airlines
Deal found 11/4$333
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Thu 12/185:30 amPWM - GCM
1 stop11h 05mUnited Airlines
Thu 12/252:25 pmGCM - PWM
1 stop8h 57mUnited Airlines
Deal found 11/3$420
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Fri 12/196:46 pmPWM - GCM
2 stops18h 59mUnited Airlines
Fri 12/262:25 pmGCM - PWM
1 stop8h 57mUnited Airlines
Deal found 11/4$640
This American Airlines deal was found by Cheapflights users on 11/4. 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.
Fri 12/196:00 amPWM - GCM
2 stops8h 49mAmerican Airlines
Fri 12/267:30 amGCM - PWM
2 stops15h 21mAmerican Airlines
Deal found 11/4$678
This American Airlines deal was found by Cheapflights users on 11/4. 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 12/216:41 pmPWM - GCM
2 stops17h 16mAmerican Airlines
Fri 1/27:30 amGCM - PWM
2 stops9h 09mAmerican Airlines
Deal found 11/4$907
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/217:01 pmPWM - GCM
2 stops21h 34mUnited Airlines
Fri 1/25:10 pmGCM - PWM
1 stop16h 34mUnited Airlines
Deal found 11/3$956

Cheap 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 November 4, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$320
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$847
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 Grand Cayman
Search Deals
Highest demand for flights based on searches. 27% potential increase in price ($266 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($73 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 4, 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

7:00 am-8:25 pm

2 stops13h 25m

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 12/18

5:30 am-4:35 pm

1 stop11h 05m

George Town Owen Roberts Intl

Thu 12/25

2:25 pm-11:22 pm

1 stop8h 57m

$420

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 1/27

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sun 2/1

2:50 pm-2:39 pm

1 stop23h 49m

$429

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Mon 4/6

5:20 pm-12:45 pm

2 stops20h 25m

George Town Owen Roberts Intl

Sun 4/12

1:15 pm-11:34 am

2 stops21h 19m

$494

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 3/10

5:52 am-2:20 pm

2 stops9h 28m

George Town Owen Roberts Intl

Wed 3/11

3:35 pm-10:30 pm

2 stops29h 55m

$532

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 3/10

6:00 am-12:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Wed 3/11

4:45 pm-11:11 pm

2 stops29h 26m

$536

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

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, November is the cheapest month in which you can book a flight from Portland, Maine to Grand Cayman (average of $235). 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 November 4, 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
8,003 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Overall

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
8,003 reviews
Delta
7.9
Good
8,003 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Overall

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
9,002 reviews
Delta
7.9
Good
8,003 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Overall

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
11,040 reviews
Delta
7.9
Good
8,003 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Overall

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 $420, American Airlines can have you in Grand Cayman from Portland, Maine in 11h 05m. 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, November is the cheapest month in which you can book a flight from Portland, Maine to Grand Cayman (average of $235). 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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$504Average$622FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$506Average$586FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$527Average$681FlexibilityNo cancel feeOn-time69%

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