HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Grand Cayman

$394+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Grand Cayman with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 14, 2025.

Round-trip from

$394
(Delta)

Popular in

December

Cheapest in

January

Average price

$587
From Portland to Grand Cayman
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($204 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($60 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/12. 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.
Wed 11/195:41 amPWM - GCM
2 stops8h 36mAmerican Airlines
Wed 12/31:40 pmGCM - PWM
1 stop8h 44mAmerican Airlines
Deal found 8/12$467
This American Airlines deal was found by Cheapflights users on 8/14. 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 11/155:19 pmPWM - GCM
2 stops19h 21mAmerican Airlines
Sat 11/221:10 pmGCM - PWM
1 stop9h 37mAmerican Airlines
Deal found 8/14$469
This Delta deal was found by Cheapflights users on 8/12. 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.
Wed 11/195:40 amPWM - GCM
1 stop6h 57mDelta
Wed 12/32:02 pmGCM - PWM
1 stop7h 57mDelta
Deal found 8/12$508
This United Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 11/159:54 amPWM - GCM
1 stop6h 41mUnited Airlines
Sat 11/225:30 pmGCM - PWM
1 stop6h 29mUnited Airlines
Deal found 8/14$536
This Delta deal was found by Cheapflights users on 8/14. 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 8/14$549
This American Airlines deal was found by Cheapflights users on 8/12. 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
1 stop18h 20mAmerican Airlines
Sat 9/2012:25 pmGCM - PWM
1 stop9h 04mAmerican Airlines
Deal found 8/12$644
This American Airlines deal was found by Cheapflights users on 8/14. 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 12/216:00 amPWM - GCM
2 stops10h 00mAmerican Airlines
Fri 1/24:15 pmGCM - PWM
2 stops19h 40mAmerican Airlines
Deal found 8/14$899
This Delta deal was found by Cheapflights users on 8/13. 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 12/215:40 amPWM - GCM
1 stop8h 40mDelta
Fri 1/23:45 pmGCM - PWM
1 stop8h 29mDelta
Deal found 8/13$975

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 August 14, 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 1/20

5:30 am-12:35 pm

1 stop7h 05m

George Town Owen Roberts Intl

Tue 1/27

2:00 pm-9:59 pm

1 stop7h 59m

$394

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 1/20

4:16 pm-11:41 am

2 stops19h 25m

George Town Owen Roberts Intl

Tue 1/27

2:15 pm-12:05 pm

2 stops21h 50m

$398

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 1/13

4:50 pm-12:00 pm

2 stops19h 10m

George Town Owen Roberts Intl

Tue 2/3

2:15 pm-12:05 pm

2 stops21h 50m

$398

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 1/13

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Tue 2/3

2:25 pm-11:17 pm

1 stop8h 52m

$429

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

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 $467). Flying from Portland, Maine to Grand Cayman 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 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 August 14, 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
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

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
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

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!
United Airlines
7.4
Good
8,916 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

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
7,980 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

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 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.

  • 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 $467). Flying from Portland, Maine to Grand Cayman 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

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 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$386Average$586FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$469Average$617FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$510Average$615FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.