HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Cayman Islands

$89+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Maine to Cayman Islands 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 Maine to Cayman Islands

Keep the following information in mind while searching for Maine to Cayman Islands flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$294
(United Airlines)

One-way from

$89
(JetBlue)
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

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 February 20, 2025.

This United Airlines deal was found by Cheapflights users on 2/19. 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 3/127:36 pmBOS - GCM
2 stops17h 39mUnited Airlines
Tue 3/184:25 pmGCM - BOS
2 stops17h 34mUnited Airlines
Deal found 2/19$294
This American Airlines deal was found by Cheapflights users on 2/19. 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 3/197:11 amBOS - GCM
1 stop8h 23mAmerican Airlines
Wed 3/2612:45 pmGCM - BOS
2 stops8h 58mAmerican Airlines
Deal found 2/19$296
This Delta deal was found by Cheapflights users on 2/19. 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 3/205:40 amBOS - GCM
1 stop6h 58mDelta
Mon 3/241:03 pmGCM - BOS
1 stop11h 02mDelta
Deal found 2/19$330
This JetBlue deal was found by Cheapflights users on 2/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/125:20 amBOS - GCM
1 stop6h 50mJetBlue
Wed 3/191:52 pmGCM - BOS
Nonstop4h 07mJetBlue
Deal found 2/19$331
This Air Canada deal was found by Cheapflights users on 2/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/16:00 amBOS - GCM
1 stop6h 55mAir Canada
Mon 5/512:50 pmGCM - BOS
2 stops24h 42mAir Canada
Deal found 2/18$425
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/411:33 amBOS - GCM
1 stop28h 37mMultiple Airlines
Sun 3/92:00 pmGCM - BOS
1 stop17h 52mMultiple Airlines
Deal found 2/18$451
This United Airlines deal was found by Cheapflights users on 2/20. 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 4/76:15 amPWM - GCM
1 stop6h 30mUnited Airlines
Fri 4/111:10 pmGCM - PWM
1 stop9h 17mUnited Airlines
Deal found 2/20$538
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Mon 3/174:11 pmPWM - GCM
2 stops20h 34mAmerican Airlines
Sun 3/232:25 pmGCM - PWM
2 stops20h 40mAmerican Airlines
Deal found 2/19$551
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/208:20 amBOS - CYB
2 stops34h 30mMultiple Airlines
Sun 3/233:55 pmCYB - BOS
2 stops31h 03mMultiple Airlines
Deal found 2/19$605
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/71:02 pmPWM - GCM
2 stops25h 28mMultiple Airlines
Fri 4/1111:05 amGCM - PWM
3 stops31h 04mMultiple Airlines
Deal found 2/20$1,117

Find flights from Maine to Cayman Islands within your budget

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 February 20, 2025.

Fly from

Maine

Fly to

Cayman Islands

Route

Depart

Return

Price

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 3/12

7:36 pm-12:15 pm

2 stops17h 39m

George Town Owen Roberts Intl

Tue 3/18

4:25 pm-10:59 am

2 stops17h 34m

$294

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 3/19

7:11 am-2:34 pm

1 stop8h 23m

George Town Owen Roberts Intl

Wed 3/26

12:45 pm-10:43 pm

2 stops8h 58m

$296

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 3/10

9:47 am-1:16 pm

Nonstop4h 29m

George Town Owen Roberts Intl

Wed 3/19

1:52 pm-6:59 pm

Nonstop4h 07m

$316

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 3/20

5:40 am-11:38 am

1 stop6h 58m

George Town Owen Roberts Intl

Tue 3/25

1:03 pm-1:05 am

1 stop11h 02m

$330

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 5/1

6:00 am-11:55 am

1 stop6h 55m

George Town Owen Roberts Intl

Mon 5/5

12:50 pm-10:03 am

1 stop20h 13m

$425

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 3/4

11:33 am-4:10 pm

1 stop28h 37m

George Town Owen Roberts Intl

Sun 3/9

2:00 pm-8:52 am

1 stop17h 52m

$451

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Mon 4/7

6:15 am-11:45 am

1 stop6h 30m

George Town Owen Roberts Intl

Fri 4/11

1:10 pm-11:27 pm

1 stop9h 17m

$538

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Mon 3/17

4:11 pm-11:45 am

2 stops20h 34m

George Town Owen Roberts Intl

Sun 3/23

2:25 pm-12:05 pm

2 stops20h 40m

$551

BostonCayman Brac

BOS - CYB

BOSCYB

Boston Logan Intl

Thu 3/20

8:20 am-5:50 pm

2 stops34h 30m

Cayman Brac Gerrard-Smith

Sun 3/23

3:55 pm-11:58 pm

2 stops31h 03m

$605

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Mon 4/7

1:02 pm-1:30 pm

2 stops25h 28m

George Town Owen Roberts Intl

Fri 4/11

11:05 am-7:09 pm

3 stops31h 04m

$1,117

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 18 results
1
2

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.

Travel insights for flights from Maine to Cayman Islands

Get recent, data-driven insights about flights from Maine to Cayman Islands including ideal travel times, pricing trends, and more.
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. 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 Cayman Islands. Reviews last updated February 20, 2025.
Read reviews from past customers who have flown Southwest, Delta and JetBlue from Maine to Cayman Islands. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

  • What are the cheapest airlines to fly from Maine to Cayman Islands one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $89. Users have also found prices from $94 and $104 on American Airlines and Delta, respectively.

  • 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.

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

    Currently, January is the cheapest month in which you can book a flight from Maine to Cayman Islands (average of $467). Flying from 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

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 Maine to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
John F Kennedy Intl to Punta Cana flights
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
Boston to Luis Munoz Marin Intl flights
O'Hare Intl to Luis Munoz Marin Intl flights
Newark to Punta Cana flights
Philadelphia to Luis Munoz Marin Intl flights
Newark to Santo Domingo flights
Dulles Intl to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
Newark to Oranjestad flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
John F Kennedy Intl to Montego Bay flights
Baltimore to Luis Munoz Marin Intl flights
Newark to Montego Bay flights
John F Kennedy Intl to Oranjestad flights
Reagan-National to Luis Munoz Marin Intl flights
Newark to Nassau flights
Orlando to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
John F Kennedy Intl to Simpson Bay flights
Atlanta to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
Newark to Simpson Bay flights
LaGuardia to Punta Cana flights
Dulles Intl to Punta Cana flights
Tampa to Luis Munoz Marin Intl flights
Boston to Oranjestad flights
O'Hare Intl to Punta Cana flights
John F Kennedy Intl to Nassau flights
Atlanta to Punta Cana flights
Philadelphia to Punta Cana flights
John F Kennedy Intl to Port of Spain flights
LaGuardia to Oranjestad flights
LaGuardia to Montego Bay flights
John F Kennedy Intl to Saint Thomas Island flights
Miami to Luis Munoz Marin Intl flights
Atlanta to Montego Bay flights
Newark to Providenciales flights
John F Kennedy Intl to Kingston flights
Boston to Punta Cana flights
John F Kennedy Intl to Bridgetown flights
Raleigh to Luis Munoz Marin Intl flights
Hobby to Luis Munoz Marin Intl flights
Baltimore to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
LaGuardia to Nassau flights

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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$386Average$467FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$467Average$617FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$547Average$704FlexibilityNo 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.