$189+ Cheap flights from Portland, ME (PWM) to the Cayman Islands
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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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Find cheap flights from Portland 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 Portland to Cayman Islands
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to Cayman IslandsExplore the most affordable flight options available from Portland to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
Explore the most affordable flight options available from Portland to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
This American Airlines deal was found by Cheapflights users on 9/19. 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.
Fri 11/276:47 pm -
2 stops17h 18m
Fri 12/113:45 pm -
2 stops18h 52m
Deal found 9/19![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 9/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:38 pm -
2 stops18h 49m
Mon 10/512:35 pm -
1 stop9h 01m
Deal found 9/20![American Airlines logo]()
$449
This American Airlines deal was found by Cheapflights users on 9/21. 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 11/77:10 am -
1 stop28h 13m
Fri 11/133:45 pm -
2 stops17h 49m
Deal found 9/21![American Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Thu 10/16:55 pm -
2 stops42h 30m
Sun 10/41:35 pm -
2 stops18h 33m
Deal found 9/21![United Airlines logo]()
$493
This United Airlines deal was found by Cheapflights users on 9/22. 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 10/315:08 pm -
2 stops24h 22m
Wed 11/45:45 pm -
2 stops20h 31m
Deal found 9/22![United Airlines logo]()
$552
This Delta deal was found by Cheapflights users on 9/21. 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.
Fri 10/26:00 am -
1 stop6h 40m
Mon 10/51:00 pm -
1 stop9h 28m
Deal found 9/21![Delta logo]()
$556
This United Airlines deal was found by Cheapflights users on 9/22. 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 11/235:08 pm -
2 stops23h 22m
Mon 11/305:45 pm -
2 stops44h 52m
Deal found 9/22![United Airlines logo]()
$599
This American Airlines deal was found by Cheapflights users on 9/19. 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.
Thu 10/157:26 pm -
2 stops17h 04m
Sun 10/182:10 pm -
2 stops8h 49m
Deal found 9/19![American Airlines logo]()
$751
Best flights from Portland to Cayman IslandsDiscover carefully curated flight deals from Portland to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
Discover carefully curated flight deals from Portland to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Fri 1/296:36 pm -
2 stops17h 12m
Mon 2/812:59 pm -
1 stop8h 30m
Deal found 9/23![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 9/19. 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.
Fri 11/276:47 pm -
1 stop17h 19m
Fri 12/113:45 pm -
2 stops17h 49m
Deal found 9/19![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 9/19. 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 1/136:36 pm -
2 stops20h 16m
Thu 2/48:21 am -
2 stops14h 25m
Deal found 9/19![American Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 9/21. 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 11/77:10 am -
1 stop28h 13m
Fri 11/133:45 pm -
2 stops17h 49m
Deal found 9/21![American Airlines logo]()
$459
Last-minute flights from Portland to Cayman IslandsDiscover last-minute flight deals from Portland to Cayman Islands. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Cayman Islands. Data last updated September 23, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Thu 10/16:55 pm -
2 stops42h 30m
Sun 10/41:35 pm -
2 stops18h 33m
Deal found 9/21![United Airlines logo]()
$493
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/15:38 pm -
2 stops18h 49m
Sun 10/412:36 pm -
1 stop9h 01m
Deal found 9/21![American Airlines logo]()
$841
This Delta deal was found by Cheapflights users on 9/21. 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 10/16:00 am -
1 stop6h 40m
Sun 10/41:00 pm -
1 stop9h 28m
Deal found 9/21![Delta logo]()
$963
This American Airlines deal was found by Cheapflights users on 9/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:38 pm -
2 stops18h 49m
Mon 10/512:35 pm -
1 stop9h 01m
Deal found 9/20![American Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 9/21. 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.
Fri 10/26:00 am -
1 stop6h 40m
Mon 10/51:00 pm -
1 stop9h 28m
Deal found 9/21![Delta logo]()
$556
This American Airlines deal was found by Cheapflights users on 9/19. 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.
Thu 10/157:26 pm -
2 stops17h 04m
Sun 10/182:10 pm -
2 stops8h 49m
Deal found 9/19![American Airlines logo]()
$751
This Delta deal was found by Cheapflights users on 9/19. 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 10/156:01 am -
1 stop6h 39m
Sun 10/1812:55 pm -
1 stop9h 40m
Deal found 9/19![Delta logo]()
$891
This United Airlines deal was found by Cheapflights users on 9/22. 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 10/315:08 pm -
2 stops24h 22m
Wed 11/45:45 pm -
2 stops20h 31m
Deal found 9/22![United Airlines logo]()
$552
One-way flights from Portland to Cayman IslandsSearch for one-way flight options from Portland to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
Search for one-way flight options from Portland to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This United Airlines deal was found by Cheapflights users on 9/23. 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 11/235:08 pm -
2 stops23h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![United Airlines logo]()
$189
This American Airlines deal was found by Cheapflights users on 9/23. 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 11/235:45 am -
2 stops14h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![American Airlines logo]()
$233
This United Airlines deal was found by Cheapflights users on 9/23. 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 11/225:08 pm -
2 stops47h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![United Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 9/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:15 am -
1 stop9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Southwest logo]()
$311
This Delta deal was found by Cheapflights users on 9/23. 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.
Mon 11/236:00 am -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta logo]()
$318
This American Airlines deal was found by Cheapflights users on 9/23. 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 11/216:47 pm -
2 stops17h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![American Airlines logo]()
$439
This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Sun 11/223:10 pm -
3 stops26h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$448
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 11/216:31 pm -
3 stops44h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Mon 11/239:48 am -
3 stops30h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$488
Find flight deals from Portland to Cayman Islands
Keep the following information in mind while searching for Portland to Cayman Islands flight deals. Data was last updated September 23, 2026.
Round-trip from | $422 (American Airlines) |
|---|---|
Popular in | April |
Cheapest in | June |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland 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 7,457,451 searches. Data last updated September 23, 2026.
Use the filters below to find and compare flights from Portland to the Cayman Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Mon 11/23
5:08 pm-4:30 pm
2 stops23h 22m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Sat 11/21
5:15 am-3:10 pm
1 stop9h 55m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$311
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Mon 11/23
6:00 am-12:25 pm
1 stop6h 25m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$318
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Sun 11/22
5:50 am-1:15 pm
1 stop7h 25m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$328
Quickest round-trip
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Mon 11/23
5:45 am-12:05 pm
1 stop6h 20m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$408
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Fri 1/29
6:36 pm-11:48 am
2 stops17h 12m
George Town Owen Roberts Intl
Mon 2/8
12:59 pm-9:29 pm
1 stop8h 30m
$422
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Fri 11/27
6:47 pm-12:06 pm
1 stop17h 19m
George Town Owen Roberts Intl
Fri 12/11
3:45 pm-9:34 am
2 stops17h 49m
$422
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Wed 1/13
6:36 pm-2:52 pm
2 stops20h 16m
George Town Owen Roberts Intl
Thu 2/4
8:21 am-10:46 pm
2 stops14h 25m
$427
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Sat 11/7
7:10 am-11:23 am
1 stop28h 13m
George Town Owen Roberts Intl
Fri 11/13
3:45 pm-9:34 am
2 stops17h 49m
$459
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Mon 11/23
9:48 am-4:05 pm
3 stops30h 17m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$488
Sorted by cheapest first
Best time to book a flight from Portland to Cayman Islands
Have a flexible travel schedule? Discover the best time to fly to Cayman Islands 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 the Cayman Islands
PWM-KY0
PWM-GCM
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 September 23, 2026.
See what other customers who have flown with Delta,United Airlines, andAmerican Airlines from Portland to the Cayman Islands have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.8
Entertainment
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.8
Entertainment
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.8
Entertainment
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.8
Entertainment
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Related info for your journey
Find useful and relevant information for your journey from Portland to Cayman Islands. 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
Complete your trip to Cayman Islands by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Portland to Cayman Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Cayman Islands flights
Browse other Portland and Cayman Islands flight options. Last updated on September 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Cayman Islands regions
Consider these flights traveling to Cayman Islands regions.
Top 3 airlines flying from Portland to Cayman Islands
Discover the top 3 airlines that operate flights from Portland 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 7,457,451 searches. Data last updated September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$480 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$200 | Average$468 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$422 | Average$607 | FlexibilityNo cancel fee | On-time71% |