$321+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Jun 4 — Jun 111
Round-trip
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 Cayman Islands
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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 May 5, 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 May 5, 2026.
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
PWM
- GCM
1 stop6h 41m
Delta
Wed 8/2612:56 pm
GCM
- PWM
1 stop8h 37m
Delta
Deal found 5/1![Delta logo]()
$321
This American Airlines deal was found by Cheapflights users on 5/3. 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 5/296:54 pm
PWM
- GCM
1 stop17h 46m
American Airlines
Mon 6/15:11 pm
GCM
- PWM
2 stops19h 27m
American Airlines
Deal found 5/3![American Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 5/3. 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 5/76:00 am
PWM
- GCM
1 stop6h 54m
Delta
Sun 5/101:19 pm
GCM
- PWM
1 stop8h 50m
Delta
Deal found 5/3![Delta logo]()
$329
This American Airlines deal was found by Cheapflights users on 5/4. 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 8/126:12 pm
PWM
- GCM
2 stops18h 18m
American Airlines
Mon 8/242:10 pm
GCM
- PWM
2 stops21h 30m
American Airlines
Deal found 5/4![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Mon 8/246:12 pm
PWM
- GCM
2 stops19h 58m
American Airlines
Fri 8/2812:00 pm
GCM
- PWM
2 stops10h 51m
American Airlines
Deal found 5/1![American Airlines logo]()
$396
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Tue 8/186:12 pm
PWM
- GCM
2 stops19h 58m
American Airlines
Sun 8/232:10 pm
GCM
- PWM
2 stops21h 30m
American Airlines
Deal found 5/1![American Airlines logo]()
$401
This American Airlines deal was found by Cheapflights users on 5/1. 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 8/237:27 am
PWM
- GCM
1 stop29h 03m
American Airlines
Thu 8/2712:00 pm
GCM
- PWM
2 stops10h 41m
American Airlines
Deal found 5/1![American Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Wed 8/196:12 pm
PWM
- GCM
2 stops19h 58m
American Airlines
Sun 8/232:10 pm
GCM
- PWM
2 stops21h 30m
American Airlines
Deal found 5/1![American Airlines logo]()
$406
This American Airlines deal was found by Cheapflights users on 5/1. 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 8/237:27 am
PWM
- GCM
1 stop29h 03m
American Airlines
Wed 8/262:10 pm
GCM
- PWM
2 stops29h 07m
American Airlines
Deal found 5/1![American Airlines logo]()
$411
This American Airlines deal was found by Cheapflights users on 5/1. 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 8/237:27 am
PWM
- GCM
2 stops28h 33m
American Airlines
Fri 8/2812:00 pm
GCM
- PWM
2 stops10h 41m
American Airlines
Deal found 5/1![American Airlines logo]()
$412
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 May 5, 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 May 5, 2026.
This American Airlines deal was found by Cheapflights users on 5/3. 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 5/296:54 pm
PWM
- GCM
2 stops19h 17m
American Airlines
Mon 6/15:11 pm
GCM
- PWM
2 stops19h 27m
American Airlines
Deal found 5/3![American Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
PWM
- GCM
1 stop6h 41m
Delta
Fri 8/2812:56 pm
GCM
- PWM
1 stop8h 37m
Delta
Deal found 5/1![Delta logo]()
$481
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Thu 8/65:15 am
PWM
- GCM
2 stops32h 15m
United Airlines
Mon 8/101:35 pm
GCM
- PWM
2 stops33h 24m
United Airlines
Deal found 5/1![United Airlines logo]()
$521
This American Airlines deal was found by Cheapflights users on 5/4. 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 8/126:12 pm
PWM
- GCM
2 stops18h 18m
American Airlines
Mon 8/242:10 pm
GCM
- PWM
2 stops21h 30m
American Airlines
Deal found 5/4![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/15:57 pm
PWM
- GCM
2 stops18h 04m
American Airlines
Fri 6/512:01 pm
GCM
- PWM
2 stops9h 45m
American Airlines
Deal found 4/30![American Airlines logo]()
$440
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Wed 8/55:15 am
PWM
- GCM
2 stops32h 15m
United Airlines
Sat 8/84:45 pm
GCM
- PWM
2 stops19h 40m
United Airlines
Deal found 5/1![United Airlines logo]()
$548
This American Airlines deal was found by Cheapflights users on 5/2. 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.
Thu 10/157:20 pm
PWM
- GCM
1 stop16h 40m
American Airlines
Tue 10/201:25 pm
GCM
- PWM
2 stops8h 59m
American Airlines
Deal found 5/2![American Airlines logo]()
$486
This American Airlines deal was found by Cheapflights users on 5/5. 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 6/147:58 am
PWM
- GCM
2 stops9h 13m
American Airlines
Wed 6/1712:33 pm
GCM
- PWM
1 stop9h 13m
American Airlines
Deal found 5/5![American Airlines logo]()
$554
Last-minute flights from Portland to Cayman IslandsDiscover last-minute flight deals from Portland to Cayman Islands. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Cayman Islands. Data last updated May 5, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/3. 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 5/76:00 am
PWM
- GCM
1 stop6h 54m
Delta
Sun 5/101:19 pm
GCM
- PWM
1 stop8h 50m
Delta
Deal found 5/3![Delta logo]()
$329
This American Airlines deal was found by Cheapflights users on 5/3. 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 5/76:01 pm
PWM
- GCM
2 stops18h 30m
American Airlines
Sun 5/1012:35 pm
GCM
- PWM
1 stop9h 11m
American Airlines
Deal found 5/3![American Airlines logo]()
$449
This American Airlines deal was found by Cheapflights users on 5/3. 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 5/296:54 pm
PWM
- GCM
1 stop17h 46m
American Airlines
Mon 6/15:11 pm
GCM
- PWM
2 stops19h 27m
American Airlines
Deal found 5/3![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/15:57 pm
PWM
- GCM
2 stops18h 04m
American Airlines
Fri 6/512:01 pm
GCM
- PWM
2 stops9h 45m
American Airlines
Deal found 4/30![American Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 5/5. 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 6/147:58 am
PWM
- GCM
2 stops9h 13m
American Airlines
Wed 6/1712:33 pm
GCM
- PWM
1 stop9h 13m
American Airlines
Deal found 5/5![American Airlines logo]()
$554
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 May 5, 2026.
Search for one-way flight options from Portland to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This business-class.com deal was found by Cheapflights users on 5/2. 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 business-class.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:00 am
PWM
- GCM
2 stops10h 35m
Copa Airlines
Deal found 5/2![Copa Airlines logo]()
$1,477
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 May 5, 2026.
Round-trip from | $321 (Delta) |
|---|---|
Popular in | November |
Cheapest in | March |
Average price | $510 |
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 May 5, 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 5/29
6:54 pm-1:11 pm
2 stops19h 17m
George Town Owen Roberts Intl
Mon 6/1
5:11 pm-1:38 pm
2 stops19h 27m
$326
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Wed 8/12
6:12 pm-11:30 am
2 stops18h 18m
George Town Owen Roberts Intl
Mon 8/24
2:10 pm-12:40 pm
2 stops21h 30m
$331
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Mon 6/1
5:57 pm-11:01 am
2 stops18h 04m
George Town Owen Roberts Intl
Fri 6/5
12:01 pm-10:46 pm
2 stops9h 45m
$440
Quickest round-trip
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Tue 8/25
6:00 am-11:41 am
1 stop6h 41m
George Town Owen Roberts Intl
Fri 8/28
12:56 pm-10:33 pm
1 stop8h 37m
$481
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Thu 10/15
7:20 pm-11:00 am
1 stop16h 40m
George Town Owen Roberts Intl
Tue 10/20
1:25 pm-11:24 pm
2 stops8h 59m
$486
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Thu 8/6
5:15 am-12:30 pm
2 stops32h 15m
George Town Owen Roberts Intl
Mon 8/10
1:35 pm-11:59 pm
2 stops33h 24m
$521
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Wed 8/5
5:15 am-12:30 pm
2 stops32h 15m
George Town Owen Roberts Intl
Sat 8/8
4:45 pm-1:25 pm
2 stops19h 40m
$548
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sun 6/14
7:58 am-4:11 pm
2 stops9h 13m
George Town Owen Roberts Intl
Wed 6/17
12:33 pm-10:46 pm
1 stop9h 13m
$554
Cheapest one-way
Quickest one-way
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sat 5/30
6:00 am-3:35 pm
2 stops10h 35m
$1,477
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 May 5, 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.
Entertainment
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.9
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Entertainment
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.9
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Entertainment
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.9
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Entertainment
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.9
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
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
See prices for flight routes from nearby airports that may be better suited for you.
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 May 5, 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 May 5, 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$587 | FlexibilityNo cancel fee | On-time71% |