$367+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Jul 8 — Jul 151
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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Cheapest
Best
Last-minute
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 8, 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 8, 2026.
This United Airlines deal was found by Cheapflights users on 6/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/34:48 pm
PWM
- GCM
2 stops23h 42m
United Airlines
Tue 12/85:45 pm
GCM
- PWM
2 stops19h 53m
United Airlines
Deal found 6/4![United Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 6/4. 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.
Thu 12/37:11 am
PWM
- GCM
1 stop7h 13m
American Airlines
Tue 12/89:00 am
GCM
- PWM
2 stops14h 37m
American Airlines
Deal found 6/4![American Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 6/4. 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.
Sun 6/147:28 pm
PWM
- GCM
2 stops19h 07m
American Airlines
Wed 6/1712:01 pm
GCM
- PWM
2 stops11h 41m
American Airlines
Deal found 6/4![American Airlines logo]()
$606
This United Airlines deal was found by Cheapflights users on 6/8. 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 6/146:00 am
PWM
- GCM
2 stops31h 30m
United Airlines
Wed 6/171:35 pm
GCM
- PWM
2 stops18h 39m
United Airlines
Deal found 6/8![United Airlines logo]()
$756
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 8, 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 8, 2026.
This United Airlines deal was found by Cheapflights users on 6/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/34:48 pm
PWM
- GCM
2 stops23h 42m
United Airlines
Tue 12/85:45 pm
GCM
- PWM
2 stops19h 53m
United Airlines
Deal found 6/4![United Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 6/4. 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.
Thu 12/37:11 am
PWM
- GCM
1 stop7h 13m
American Airlines
Tue 12/83:14 pm
GCM
- PWM
1 stop7h 20m
American Airlines
Deal found 6/4![American Airlines logo]()
$561
Last-minute flights from Portland to Cayman IslandsDiscover last-minute flight deals from Portland to Cayman Islands. Data last updated June 8, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Cayman Islands. Data last updated June 8, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/4. 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.
Sun 6/147:28 pm
PWM
- GCM
2 stops19h 07m
American Airlines
Wed 6/1712:01 pm
GCM
- PWM
2 stops11h 41m
American Airlines
Deal found 6/4![American Airlines logo]()
$606
This United Airlines deal was found by Cheapflights users on 6/8. 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 6/146:00 am
PWM
- GCM
2 stops31h 30m
United Airlines
Wed 6/171:35 pm
GCM
- PWM
2 stops18h 39m
United Airlines
Deal found 6/8![United Airlines logo]()
$756
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 8, 2026.
Round-trip from | $367 (United Airlines) |
|---|---|
Popular in | November |
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 8, 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
Thu 12/3
4:48 pm-4:30 pm
2 stops23h 42m
George Town Owen Roberts Intl
Tue 12/8
5:45 pm-1:38 pm
2 stops19h 53m
$367
Quickest round-trip
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Thu 12/3
7:11 am-2:24 pm
1 stop7h 13m
George Town Owen Roberts Intl
Tue 12/8
3:14 pm-10:34 pm
1 stop7h 20m
$561
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 June 8, 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.
Food
7.2
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.8
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.8
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.8
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.8
Overall
7.9
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.
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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 June 8, 2026.
Popular flight searches
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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 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$200 | Average$468 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$439 | Average$574 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$480 | Average$608 | FlexibilityNo cancel fee | On-timeN/A |