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Cayman Islands

$88+ Cheap flights from Maine to the Cayman Islands

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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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Find flight deals from Maine to Cayman Islands

Cheapest flights from Maine to Cayman Islands
Explore the most affordable flight options available from Maine to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2025.

This American Airlines deal was found by Cheapflights users on 10/26. 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 11/295:40 amBOS - GCM
1 stop5h 54mAmerican Airlines
Sat 12/61:01 pmGCM - BOS
1 stop7h 04mAmerican Airlines
Deal found 10/26$273
This United Airlines deal was found by Cheapflights users on 10/26. 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 12/316:45 amBOS - GCM
1 stop6h 30mUnited Airlines
Mon 1/122:25 pmGCM - BOS
1 stop7h 27mUnited Airlines
Deal found 10/26$277
This American Airlines deal was found by Cheapflights users on 10/26. 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 12/65:45 amBOS - GCM
1 stop6h 16mAmerican Airlines
Tue 12/98:45 amGCM - BOS
1 stop14h 23mAmerican Airlines
Deal found 10/26$280
This United Airlines deal was found by Cheapflights users on 10/26. 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.
Mon 10/277:00 amBOS - GCM
1 stop9h 30mUnited Airlines
Sun 11/22:25 pmGCM - BOS
1 stop8h 27mUnited Airlines
Deal found 10/26$284
This American Airlines deal was found by Cheapflights users on 10/25. 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 12/66:00 amBOS - GCM
2 stops8h 22mAmerican Airlines
Sat 12/131:01 pmGCM - BOS
1 stop9h 42mAmerican Airlines
Deal found 10/25$285
This American Airlines deal was found by Cheapflights users on 10/26. 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 12/102:24 pmBOS - GCM
1 stop24h 00mAmerican Airlines
Wed 12/173:45 pmGCM - BOS
1 stop9h 14mAmerican Airlines
Deal found 10/26$287
This United Airlines deal was found by Cheapflights users on 10/26. 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 10/317:00 amBOS - GCM
1 stop9h 30mUnited Airlines
Tue 11/45:45 pmGCM - BOS
2 stops16h 49mUnited Airlines
Deal found 10/26$289
This American Airlines deal was found by Cheapflights users on 10/26. 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 12/25:18 pmBOS - GCM
1 stop18h 47mAmerican Airlines
Mon 12/83:45 pmGCM - BOS
2 stops8h 30mAmerican Airlines
Deal found 10/26$291
This United Airlines deal was found by Cheapflights users on 10/25. 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 11/47:00 amBOS - GCM
1 stop9h 30mUnited Airlines
Wed 11/125:45 pmGCM - BOS
1 stop23h 58mUnited Airlines
Deal found 10/25$292
This United Airlines deal was found by Cheapflights users on 10/25. 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 12/245:20 amBOS - GCM
1 stop11h 15mUnited Airlines
Mon 12/292:50 pmGCM - BOS
1 stop9h 55mUnited Airlines
Deal found 10/25$298
This American Airlines deal was found by Cheapflights users on 10/26. 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 12/115:17 pmPWM - GCM
2 stops20h 49mAmerican Airlines
Tue 12/161:25 pmGCM - PWM
2 stops10h 12mAmerican Airlines
Deal found 10/26$315
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:00 amPWM - GCM
1 stop6h 44mDelta
Mon 11/101:50 pmGCM - PWM
1 stop8h 29mDelta
Deal found 10/27$328

Cheap flight deals from Maine to Cayman Islands

Keep the following information in mind while searching for Maine to Cayman Islands flight deals. Data was last updated October 27, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$273
(American Airlines)

One-way from

$88
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$545
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 Maine to Cayman Islands
Search Deals
One-way flight from Maine to Cayman Islands
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 October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maine 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 October 27, 2025.
Use the filters below to find and compare flights from Maine to the Cayman Islands that are best for you.

Fly from

Maine

Fly to

Cayman Islands

Route

Depart

Return

Price

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 12/31

6:45 am-1:15 pm

1 stop6h 30m

George Town Owen Roberts Intl

Mon 1/12

2:25 pm-9:52 pm

1 stop7h 27m

$277

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 2/28

7:19 pm-1:45 pm

2 stops18h 26m

George Town Owen Roberts Intl

Thu 3/5

2:25 pm-9:41 pm

1 stop7h 16m

$284

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 11/15

5:30 am-4:35 pm

1 stop11h 05m

George Town Owen Roberts Intl

Sat 11/22

2:25 pm-9:59 pm

1 stop7h 34m

$284

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 1/10

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sat 1/17

5:30 pm-11:49 pm

1 stop6h 19m

$284

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 12/8

7:00 am-4:30 pm

1 stop9h 30m

George Town Owen Roberts Intl

Sat 12/13

5:45 pm-12:21 pm

1 stop18h 36m

$284

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 12/6

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sat 12/13

5:45 pm-12:21 pm

1 stop18h 36m

$284

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 1/5

6:01 am-1:45 pm

1 stop7h 44m

George Town Owen Roberts Intl

Fri 1/9

2:25 pm-9:52 pm

1 stop7h 27m

$284

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 1/17

7:22 pm-1:15 pm

2 stops17h 53m

George Town Owen Roberts Intl

Sat 1/24

5:30 pm-11:49 pm

1 stop6h 19m

$284

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 2/4

7:07 pm-1:15 pm

2 stops18h 08m

George Town Owen Roberts Intl

Tue 2/10

2:25 pm-11:49 pm

2 stops9h 24m

$289

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 1/2

9:30 am-4:35 pm

1 stop7h 05m

George Town Owen Roberts Intl

Thu 1/8

2:25 pm-11:49 pm

2 stops9h 24m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Showing 1-10 of 29 results
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Best time to book a flight from Maine to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Maine 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 Maine to the Cayman Islands
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Maine to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Maine to Cayman Islands?

    For as low as $277, United Airlines can have you in Cayman Islands from Maine in 6h 30m. There are 1704 mi between Maine and Cayman Islands. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

  • How can I find direct flights from Maine to Cayman Islands?

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

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

    Yes. Cheapflights offers flight deals from Maine 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Maine to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Maine to Cayman Islands

Discover the top 3 airlines that operate flights from Maine 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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$504Average$622FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$506Average$586FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$536Average$681FlexibilityNo cancel feeOn-time69%

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