$137+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
May 10 — May 171
Round-trip
1 adult, Economy
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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
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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
Cheapest
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 April 10, 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 April 10, 2026.
This American Airlines deal was found by Cheapflights users on 4/9. 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 9/66:50 pm
PWM
- GCM
2 stops19h 20m
American Airlines
Sat 9/121:20 pm
GCM
- PWM
2 stops21h 11m
American Airlines
Deal found 4/9![American Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 4/5. 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 11/75:37 pm
PWM
- GCM
2 stops18h 21m
American Airlines
Wed 11/114:10 pm
GCM
- PWM
2 stops19h 39m
American Airlines
Deal found 4/5![American Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 4/9. 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 6/106:54 pm
PWM
- GCM
2 stops17h 07m
American Airlines
Fri 6/195:12 pm
GCM
- PWM
2 stops20h 12m
American Airlines
Deal found 4/9![American Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 4/9. 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 6/106:00 am
PWM
- GCM
1 stop6h 34m
Delta
Fri 6/1912:59 pm
GCM
- PWM
1 stop9h 16m
Delta
Deal found 4/9![Delta logo]()
$493
This United Airlines deal was found by Cheapflights users on 4/5. 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 4/66:04 am
PWM
- GCM
1 stop7h 41m
United Airlines
Sun 4/121:50 pm
GCM
- PWM
1 stop30h 50m
United Airlines
Deal found 4/5![United Airlines logo]()
$509
This American Airlines deal was found by Cheapflights users on 4/6. 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 6/146:54 pm
PWM
- GCM
2 stops17h 07m
American Airlines
Wed 6/175:12 pm
GCM
- PWM
2 stops20h 12m
American Airlines
Deal found 4/6![American Airlines logo]()
$550
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 April 10, 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 April 10, 2026.
This American Airlines deal was found by Cheapflights users on 4/9. 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 9/611:57 am
PWM
- GCM
1 stop24h 28m
American Airlines
Sat 9/121:20 pm
GCM
- PWM
2 stops21h 11m
American Airlines
Deal found 4/9![American Airlines logo]()
$461
This Delta deal was found by Cheapflights users on 4/9. 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 6/106:00 am
PWM
- GCM
1 stop6h 34m
Delta
Fri 6/1912:59 pm
GCM
- PWM
1 stop9h 16m
Delta
Deal found 4/9![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 4/9. 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 9/66:00 am
PWM
- GCM
1 stop6h 41m
Delta
Sat 9/1212:55 pm
GCM
- PWM
1 stop8h 38m
Delta
Deal found 4/9![Delta logo]()
$493
This American Airlines deal was found by Cheapflights users on 4/6. 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 6/146:54 pm
PWM
- GCM
2 stops17h 07m
American Airlines
Wed 6/175:12 pm
GCM
- PWM
2 stops20h 12m
American Airlines
Deal found 4/6![American Airlines logo]()
$550
Last-minute flights from Portland to Grand CaymanDiscover last-minute flight deals from Portland to Grand Cayman. Data last updated April 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Grand Cayman. Data last updated April 10, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/6. 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 4/187:23 pm
PWM
- GCM
2 stops18h 47m
American Airlines
Thu 4/232:10 pm
GCM
- PWM
2 stops18h 57m
American Airlines
Deal found 4/6![American Airlines logo]()
$731
This United Airlines deal was found by Cheapflights users on 4/5. 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 4/186:00 am
PWM
- GCM
1 stop8h 30m
United Airlines
Thu 4/231:50 pm
GCM
- PWM
1 stop30h 50m
United Airlines
Deal found 4/5![United Airlines logo]()
$1,175
This United Airlines deal was found by Cheapflights users on 4/7. 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 5/227:16 pm
PWM
- GCM
2 stops18h 19m
United Airlines
Fri 5/291:35 pm
GCM
- PWM
2 stops23h 51m
United Airlines
Deal found 4/7![United Airlines logo]()
$819
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 April 10, 2026.
Search for one-way flight options from Portland to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
This American Airlines deal was found by Cheapflights users on 4/7. 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 4/256:00 am
PWM
- GCM
1 stop6h 44m
American Airlines
Deal found 4/7![American Airlines logo]()
$137
This American Airlines deal was found by Cheapflights users on 4/5. 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 7/196:59 pm
PWM
- GCM
2 stops17h 26m
American Airlines
Deal found 4/5![American Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 4/7. 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.
Sat 4/256:18 pm
PWM
- GCM
3 stops42h 17m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 4/5. 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 7/195:15 am
PWM
- GCM
3 stops32h 15m
United Airlines
Deal found 4/5![United Airlines logo]()
$723
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 April 10, 2026.
Round-trip from | $550 (American Airlines) |
|---|---|
One-way from | $137 (American Airlines) |
Popular in | November |
Cheapest in | March |
Average price | $654 |
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 April 10, 2026.
Use the filters below to find and compare flights from Portland to Grand Cayman that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sun 9/6
11:57 am-11:25 am
1 stop24h 28m
George Town Owen Roberts Intl
Sat 9/12
1:20 pm-11:31 am
2 stops21h 11m
$461
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Wed 6/10
6:00 am-11:34 am
1 stop6h 34m
George Town Owen Roberts Intl
Fri 6/19
12:59 pm-11:15 pm
1 stop9h 16m
$493
Quickest round-trip
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sun 9/6
6:00 am-11:41 am
1 stop6h 41m
George Town Owen Roberts Intl
Sat 9/12
12:55 pm-10:33 pm
1 stop8h 38m
$493
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sun 6/14
6:54 pm-11:01 am
2 stops17h 07m
George Town Owen Roberts Intl
Wed 6/17
5:12 pm-2:24 pm
2 stops20h 12m
$550
Cheapest one-way
Quickest one-way
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sat 4/25
6:00 am-11:44 am
1 stop6h 44m
$137
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sat 4/25
6:18 pm-11:35 am
3 stops42h 17m
$318
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sun 7/19
6:00 pm-11:25 am
1 stop18h 25m
$447
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sun 7/19
5:15 am-12:30 pm
3 stops32h 15m
$723
Sorted by cheapest first
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 $393). 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 April 10, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican 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
Entertainment
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Entertainment
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Entertainment
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Entertainment
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Overall
7.9
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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Complete your trip
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Portland and Grand Cayman flights
Browse other Portland and Grand Cayman flight options. Last updated on April 10, 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 April 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$200 | Average$468 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$480 | Average$608 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$504 | Average$586 | FlexibilityNo cancel fee | On-time71% |