$102+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Mar 5 — Mar 121
1 adult, Economy
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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
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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
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Best
Last-minute
One-way
Cheapest flights from Portland to Grand CaymanExplore 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 February 3, 2026.
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 February 3, 2026.
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/255:40 pm
PWM
- GCM
2 stops18h 10m
American Airlines
Wed 3/117:45 am
GCM
- PWM
2 stops14h 49m
American Airlines
Deal found 2/2![American Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/256:00 am
PWM
- GCM
1 stop7h 15m
United Airlines
Wed 3/111:25 pm
GCM
- PWM
1 stop8h 39m
United Airlines
Deal found 2/2![United Airlines logo]()
$428
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/146:49 pm
PWM
- GCM
2 stops17h 19m
American Airlines
Thu 2/1912:50 pm
GCM
- PWM
2 stops11h 00m
American Airlines
Deal found 2/2![American Airlines logo]()
$507
This American Airlines deal was found by Cheapflights users on 2/2. 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 8/26:00 am
PWM
- GCM
2 stops30h 20m
American Airlines
Sat 8/82:55 pm
GCM
- PWM
2 stops20h 22m
American Airlines
Deal found 2/2![American Airlines logo]()
$531
This American Airlines deal was found by Cheapflights users on 2/2. 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 8/17:23 am
PWM
- GCM
2 stops28h 37m
American Airlines
Sat 8/82:55 pm
GCM
- PWM
2 stops20h 22m
American Airlines
Deal found 2/2![American Airlines logo]()
$533
This American Airlines deal was found by Cheapflights users on 2/2. 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 8/26:00 am
PWM
- GCM
2 stops30h 20m
American Airlines
Fri 8/712:25 pm
GCM
- PWM
2 stops28h 01m
American Airlines
Deal found 2/2![American Airlines logo]()
$549
This American Airlines deal was found by Cheapflights users on 2/2. 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 8/17:23 am
PWM
- GCM
2 stops28h 37m
American Airlines
Fri 8/712:25 pm
GCM
- PWM
2 stops28h 01m
American Airlines
Deal found 2/2![American Airlines logo]()
$552
This American Airlines deal was found by Cheapflights users on 2/1. 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 6/145:52 pm
PWM
- GCM
2 stops18h 08m
American Airlines
Wed 6/1712:20 pm
GCM
- PWM
1 stop9h 20m
American Airlines
Deal found 2/1![American Airlines logo]()
$564
This United Airlines deal was found by Cheapflights users on 2/1. 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 3/146:00 am
PWM
- GCM
1 stop6h 45m
United Airlines
Sat 3/2812:55 pm
GCM
- PWM
1 stop8h 57m
United Airlines
Deal found 2/1![United Airlines logo]()
$565
Best flights from Portland to Grand CaymanDiscover carefully curated flight deals from Portland to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from Portland to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/255:40 pm
PWM
- GCM
2 stops18h 10m
American Airlines
Wed 3/117:45 am
GCM
- PWM
2 stops14h 49m
American Airlines
Deal found 2/2![American Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/256:00 am
PWM
- GCM
1 stop7h 15m
United Airlines
Wed 3/111:25 pm
GCM
- PWM
1 stop8h 39m
United Airlines
Deal found 2/2![United Airlines logo]()
$428
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/146:49 pm
PWM
- GCM
2 stops17h 19m
American Airlines
Thu 2/198:45 am
GCM
- PWM
2 stops15h 05m
American Airlines
Deal found 2/2![American Airlines logo]()
$507
This American Airlines deal was found by Cheapflights users on 2/2. 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 8/17:23 am
PWM
- GCM
2 stops28h 37m
American Airlines
Sat 8/82:55 pm
GCM
- PWM
2 stops20h 22m
American Airlines
Deal found 2/2![American Airlines logo]()
$533
This American Airlines deal was found by Cheapflights users on 2/2. 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 8/26:00 am
PWM
- GCM
2 stops30h 20m
American Airlines
Fri 8/712:25 pm
GCM
- PWM
2 stops28h 01m
American Airlines
Deal found 2/2![American Airlines logo]()
$549
This American Airlines deal was found by Cheapflights users on 2/2. 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 8/17:23 am
PWM
- GCM
2 stops28h 37m
American Airlines
Fri 8/712:25 pm
GCM
- PWM
2 stops28h 01m
American Airlines
Deal found 2/2![American Airlines logo]()
$552
This American Airlines deal was found by Cheapflights users on 2/1. 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 6/145:52 pm
PWM
- GCM
2 stops18h 08m
American Airlines
Wed 6/1712:20 pm
GCM
- PWM
1 stop9h 20m
American Airlines
Deal found 2/1![American Airlines logo]()
$564
Last-minute flights from Portland to Grand CaymanDiscover last-minute flight deals from Portland to Grand Cayman. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Grand Cayman. Data last updated February 3, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/146:49 pm
PWM
- GCM
2 stops17h 19m
American Airlines
Thu 2/1912:50 pm
GCM
- PWM
2 stops11h 00m
American Airlines
Deal found 2/2![American Airlines logo]()
$507
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/255:40 pm
PWM
- GCM
2 stops18h 10m
American Airlines
Wed 3/117:45 am
GCM
- PWM
2 stops14h 49m
American Airlines
Deal found 2/2![American Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/256:00 am
PWM
- GCM
1 stop7h 15m
United Airlines
Wed 3/111:25 pm
GCM
- PWM
1 stop8h 39m
United Airlines
Deal found 2/2![United Airlines logo]()
$428
This United Airlines deal was found by Cheapflights users on 2/1. 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 3/146:00 am
PWM
- GCM
1 stop6h 45m
United Airlines
Sat 3/2812:55 pm
GCM
- PWM
1 stop8h 57m
United Airlines
Deal found 2/1![United Airlines logo]()
$565
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/145:57 pm
PWM
- GCM
1 stop20h 47m
American Airlines
Sat 3/282:35 pm
GCM
- PWM
2 stops19h 44m
American Airlines
Deal found 2/2![American Airlines logo]()
$616
One-way flights from Portland to Grand CaymanSearch for one-way flight options from Portland to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Portland to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/45:40 pm
PWM
- GCM
2 stops18h 10m
American Airlines
Deal found 2/2![American Airlines logo]()
$102
This Delta deal was found by Cheapflights users on 2/2. 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 3/45:31 am
PWM
- GCM
1 stop6h 58m
Delta
Deal found 2/2![Delta logo]()
$108
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 February 3, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $302 (American Airlines) |
One-way from | $102 (American Airlines) |
Popular in | November |
Cheapest in | May |
Average price | $603 |
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 February 3, 2026.
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
Wed 2/25
5:40 pm-11:50 am
2 stops18h 10m
George Town Owen Roberts Intl
Wed 3/11
7:45 am-11:34 pm
2 stops14h 49m
$302
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Wed 2/25
6:00 am-1:15 pm
1 stop7h 15m
George Town Owen Roberts Intl
Wed 3/11
1:25 pm-11:04 pm
1 stop8h 39m
$428
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sat 2/14
6:49 pm-12:08 pm
2 stops17h 19m
George Town Owen Roberts Intl
Thu 2/19
8:45 am-11:50 pm
2 stops15h 05m
$507
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sat 8/1
7:23 am-11:00 am
2 stops28h 37m
George Town Owen Roberts Intl
Sat 8/8
2:55 pm-12:17 pm
2 stops20h 22m
$533
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sun 8/2
6:00 am-11:20 am
2 stops30h 20m
George Town Owen Roberts Intl
Fri 8/7
12:25 pm-5:26 pm
2 stops28h 01m
$549
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sat 8/1
7:23 am-11:00 am
2 stops28h 37m
George Town Owen Roberts Intl
Fri 8/7
12:25 pm-5:26 pm
2 stops28h 01m
$552
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sun 6/14
5:52 pm-11:00 am
2 stops18h 08m
George Town Owen Roberts Intl
Wed 6/17
12:20 pm-10:40 pm
1 stop9h 20m
$564
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Wed 3/4
5:40 pm-11:50 am
2 stops18h 10m
$102
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Wed 3/4
5:31 am-12:29 pm
1 stop6h 58m
$108
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.
PWM-GCM
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
PWM-zzLAW
PWM-GCM
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 $72). Flying from Portland, Maine to Grand Cayman in August is currently the most expensive (average of $404). 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 February 3, 2026.
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.
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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.
Complete your trip
Complete your trip to Grand Cayman by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Grand Cayman by cabin class
Find flights from Portland to Grand Cayman, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Grand Cayman flights
Browse other Portland and Grand Cayman flight options. Last updated on February 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$200 | Average$603 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$480 | Average$608 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$510 | Average$587 | FlexibilityNo cancel fee | On-time71% |