$118+ Cheap flights from Portland, ME (PWM) 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 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Jul 19 — Jul 261
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Cayman Islands with Cheapflights
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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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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 June 19, 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 June 19, 2026.
This Delta deal was found by Cheapflights users on 6/14. 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 9/256:05 am
PWM
- GCM
1 stop6h 35m
Delta
Mon 9/2812:55 pm
GCM
- PWM
1 stop9h 30m
Delta
Deal found 6/14![Delta logo]()
$331
This American Airlines deal was found by Cheapflights users on 6/14. 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 7/35:07 pm
PWM
- GCM
1 stop18h 16m
American Airlines
Mon 7/65:10 pm
GCM
- PWM
2 stops20h 06m
American Airlines
Deal found 6/14![American Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:05 am
PWM
- GCM
1 stop6h 34m
Delta
Thu 8/271:04 pm
GCM
- PWM
1 stop9h 09m
Delta
Deal found 6/18![Delta logo]()
$341
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:25 am
PWM
- GCM
2 stops30h 06m
Delta
Mon 8/31:04 pm
GCM
- PWM
1 stop9h 09m
Delta
Deal found 6/18![Delta logo]()
$346
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:09 pm
PWM
- GCM
2 stops20h 01m
American Airlines
Wed 8/2612:30 pm
GCM
- PWM
2 stops10h 29m
American Airlines
Deal found 6/18![American Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 6/17. 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 8/156:46 pm
PWM
- GCM
2 stops17h 44m
American Airlines
Sat 8/224:00 pm
GCM
- PWM
1 stop25h 27m
American Airlines
Deal found 6/17![American Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 6/17. 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 7/296:01 pm
PWM
- GCM
1 stop18h 24m
American Airlines
Tue 8/412:33 pm
GCM
- PWM
1 stop9h 03m
American Airlines
Deal found 6/17![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 6/16. 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 7/35:07 pm
PWM
- GCM
1 stop18h 16m
American Airlines
Wed 7/812:33 pm
GCM
- PWM
1 stop9h 03m
American Airlines
Deal found 6/16![American Airlines logo]()
$401
This American Airlines deal was found by Cheapflights users on 6/16. 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 7/178:00 am
PWM
- GCM
1 stop28h 45m
American Airlines
Mon 7/205:10 pm
GCM
- PWM
2 stops20h 06m
American Airlines
Deal found 6/16![American Airlines logo]()
$413
This American Airlines deal was found by Cheapflights users on 6/16. 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 7/147:16 am
PWM
- GCM
1 stop29h 09m
American Airlines
Mon 7/205:10 pm
GCM
- PWM
2 stops20h 06m
American Airlines
Deal found 6/16![American Airlines logo]()
$414
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 June 19, 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 June 19, 2026.
This Delta deal was found by Cheapflights users on 6/14. 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 9/256:05 am
PWM
- GCM
1 stop6h 35m
Delta
Mon 9/2812:55 pm
GCM
- PWM
1 stop9h 30m
Delta
Deal found 6/14![Delta logo]()
$331
This American Airlines deal was found by Cheapflights users on 6/14. 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 9/255:18 pm
PWM
- GCM
2 stops18h 37m
American Airlines
Mon 9/2812:00 pm
GCM
- PWM
2 stops21h 17m
American Airlines
Deal found 6/14![American Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 6/14. 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 7/410:04 am
PWM
- GCM
1 stop6h 06m
United Airlines
Tue 7/71:35 pm
GCM
- PWM
2 stops23h 56m
United Airlines
Deal found 6/14![United Airlines logo]()
$561
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:57 pm
PWM
- GCM
1 stop17h 37m
Delta
Wed 7/812:56 pm
GCM
- PWM
1 stop9h 18m
Delta
Deal found 6/18![Delta logo]()
$341
This Delta deal was found by Cheapflights users on 6/16. 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 12/33:00 pm
PWM
- GCM
2 stops21h 25m
Delta
Tue 12/81:50 pm
GCM
- PWM
1 stop8h 33m
Delta
Deal found 6/16![Delta logo]()
$481
This Delta deal was found by Cheapflights users on 6/17. 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 8/276:05 am
PWM
- GCM
1 stop6h 34m
Delta
Fri 9/41:04 pm
GCM
- PWM
1 stop9h 09m
Delta
Deal found 6/17![Delta logo]()
$482
This United Airlines deal was found by Cheapflights users on 6/17. 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 7/115:15 am
PWM
- GCM
1 stop10h 55m
United Airlines
Wed 7/151:35 pm
GCM
- PWM
2 stops31h 06m
United Airlines
Deal found 6/17![United Airlines logo]()
$608
This United Airlines deal was found by Cheapflights users on 6/16. 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 7/145:00 pm
PWM
- GCM
2 stops20h 30m
United Airlines
Sat 7/254:45 pm
GCM
- PWM
2 stops24h 44m
United Airlines
Deal found 6/16![United Airlines logo]()
$691
This Delta deal was found by Cheapflights users on 6/14. 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 7/26:00 am
PWM
- GCM
1 stop6h 34m
Delta
Tue 7/712:56 pm
GCM
- PWM
1 stop9h 18m
Delta
Deal found 6/14![Delta logo]()
$641
This Delta deal was found by Cheapflights users on 6/17. 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 7/86:59 pm
PWM
- GCM
1 stop17h 32m
Delta
Thu 7/1612:56 pm
GCM
- PWM
1 stop9h 18m
Delta
Deal found 6/17![Delta logo]()
$670
Last-minute flights from Portland to Cayman IslandsDiscover last-minute flight deals from Portland to Cayman Islands. Data last updated June 19, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Cayman Islands. Data last updated June 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/196:54 pm
PWM
- GCM
2 stops19h 17m
American Airlines
Sat 6/273:35 pm
GCM
- PWM
2 stops29h 11m
American Airlines
Deal found 6/18![American Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 6/14. 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 7/36:01 pm
PWM
- GCM
2 stops17h 54m
American Airlines
Mon 7/65:10 pm
GCM
- PWM
2 stops20h 06m
American Airlines
Deal found 6/14![American Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 6/16. 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 7/35:07 pm
PWM
- GCM
1 stop18h 16m
American Airlines
Wed 7/812:33 pm
GCM
- PWM
1 stop9h 03m
American Airlines
Deal found 6/16![American Airlines logo]()
$401
This American Airlines deal was found by Cheapflights users on 6/16. 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 7/147:16 am
PWM
- GCM
1 stop29h 09m
American Airlines
Mon 7/205:10 pm
GCM
- PWM
2 stops20h 06m
American Airlines
Deal found 6/16![American Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 6/16. 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 7/178:00 am
PWM
- GCM
1 stop28h 45m
American Airlines
Mon 7/205:10 pm
GCM
- PWM
2 stops20h 06m
American Airlines
Deal found 6/16![American Airlines logo]()
$413
This American Airlines deal was found by Cheapflights users on 6/17. 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 7/296:01 pm
PWM
- GCM
1 stop18h 24m
American Airlines
Tue 8/412:33 pm
GCM
- PWM
1 stop9h 03m
American Airlines
Deal found 6/17![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:59 pm
PWM
- GCM
1 stop17h 32m
Delta
Tue 8/41:04 pm
GCM
- PWM
1 stop9h 09m
Delta
Deal found 6/18![Delta logo]()
$341
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 June 19, 2026.
Search for one-way flight options from Portland to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
This Delta deal was found by Cheapflights users on 6/17. 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 6/246:00 am
PWM
- GCM
1 stop6h 34m
Delta
Deal found 6/17![Delta logo]()
$118
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:10 am
PWM
- GCM
1 stop28h 05m
United Airlines
Deal found 6/18![United Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Wed 6/245:01 pm
PWM
- GCM
2 stops43h 34m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$447
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 June 19, 2026.
Round-trip from | $331 (Delta) |
|---|---|
One-way from | $118 (Delta) |
Popular in | December |
Cheapest in | May |
Average price | $645 |
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 2,558,603 searches. Data last updated June 19, 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 - GCM
PWMGCM
Portland
Fri 9/25
6:05 am-11:40 am
1 stop6h 35m
George Town Owen Roberts Intl
Mon 9/28
12:55 pm-11:25 pm
1 stop9h 30m
$331
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Fri 9/25
5:18 pm-10:55 am
2 stops18h 37m
George Town Owen Roberts Intl
Mon 9/28
12:00 pm-10:17 am
2 stops21h 17m
$336
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Tue 6/30
6:57 pm-11:34 am
1 stop17h 37m
George Town Owen Roberts Intl
Wed 7/8
12:56 pm-11:14 pm
1 stop9h 18m
$341
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Thu 12/3
3:00 pm-12:25 pm
2 stops21h 25m
George Town Owen Roberts Intl
Tue 12/8
1:50 pm-10:23 pm
1 stop8h 33m
$481
Quickest round-trip
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Thu 8/27
6:05 am-11:39 am
1 stop6h 34m
George Town Owen Roberts Intl
Fri 9/4
1:04 pm-11:13 pm
1 stop9h 09m
$482
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sat 7/4
10:04 am-3:10 pm
1 stop6h 06m
George Town Owen Roberts Intl
Tue 7/7
1:35 pm-2:31 pm
2 stops23h 56m
$561
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sat 7/11
5:15 am-3:10 pm
1 stop10h 55m
George Town Owen Roberts Intl
Wed 7/15
1:35 pm-9:41 pm
2 stops31h 06m
$608
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Thu 7/2
6:00 am-11:34 am
1 stop6h 34m
George Town Owen Roberts Intl
Tue 7/7
12:56 pm-11:14 pm
1 stop9h 18m
$641
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Wed 7/8
6:59 pm-11:31 am
1 stop17h 32m
George Town Owen Roberts Intl
Thu 7/16
12:56 pm-11:14 pm
1 stop9h 18m
$670
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Tue 7/14
5:00 pm-12:30 pm
2 stops20h 30m
George Town Owen Roberts Intl
Sat 7/25
4:45 pm-6:29 pm
2 stops24h 44m
$691
Showing 1-10 of 14 resultsSorted 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 June 19, 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.
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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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Alternative routes for Portland to Cayman Islands
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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.
Search flights from Portland to Cayman Islands by cabin class
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 June 19, 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 2,558,603 searches. Data last updated June 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$200 | Average$468 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$439 | Average$589 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$480 | Average$596 | FlexibilityNo cancel fee | On-timeN/A |