$186+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — GCM
Dec 9 — Dec 161
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 November 9, 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 November 9, 2026.
This American Airlines deal was found by Cheapflights users on 11/7. 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.
Fri 11/276:47 pm -
1 stop17h 19m
Fri 12/113:45 pm -
2 stops17h 43m
Deal found 11/7![American Airlines logo]()
$472
This American Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/26:44 pm -
2 stops20h 01m
Wed 12/98:15 am -
2 stops13h 25m
Deal found 11/6![American Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 11/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:01 am -
1 stop28h 25m
Thu 12/1012:21 pm -
1 stop10h 27m
Deal found 11/8![American Airlines logo]()
$569
This American Airlines deal was found by Cheapflights users on 11/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:30 am -
1 stop9h 05m
Wed 12/303:30 pm -
1 stop7h 29m
Deal found 11/8![American Airlines logo]()
$615
This United Airlines deal was found by Cheapflights users on 11/7. 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.
Tue 12/225:15 am -
2 stops32h 30m
Tue 12/295:10 pm -
2 stops15h 57m
Deal found 11/7![United Airlines logo]()
$619
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Wed 12/235:15 am -
2 stops34h 45m
Wed 12/305:45 pm -
2 stops25h 18m
Deal found 11/8![United Airlines logo]()
$622
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 November 9, 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 November 9, 2026.
This American Airlines deal was found by Cheapflights users on 11/7. 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.
Fri 11/276:47 pm -
2 stops19h 53m
Fri 12/113:45 pm -
2 stops17h 43m
Deal found 11/7![American Airlines logo]()
$472
This United Airlines deal was found by Cheapflights users on 11/7. 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.
Tue 12/225:15 am -
2 stops32h 30m
Tue 12/295:10 pm -
2 stops15h 57m
Deal found 11/7![United Airlines logo]()
$619
This American Airlines deal was found by Cheapflights users on 11/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:01 am -
1 stop28h 25m
Thu 12/103:45 pm -
2 stops17h 37m
Deal found 11/8![American Airlines logo]()
$482
This American Airlines deal was found by Cheapflights users on 11/5. 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 5/16:00 am -
1 stop6h 00m
Sat 5/84:00 pm -
1 stop18h 15m
Deal found 11/5![American Airlines logo]()
$560
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Wed 12/235:15 am -
2 stops34h 45m
Wed 12/305:45 pm -
2 stops25h 18m
Deal found 11/8![United Airlines logo]()
$622
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Mon 2/17:50 pm -
1 stop17h 25m
Thu 2/42:25 pm -
2 stops48h 26m
Deal found 11/4![United Airlines logo]()
$631
Last-minute flights from Portland to Cayman IslandsDiscover last-minute flight deals from Portland to Cayman Islands. Data last updated November 9, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Cayman Islands. Data last updated November 9, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 11/7. 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.
Fri 11/276:47 pm -
1 stop17h 19m
Fri 12/113:45 pm -
2 stops17h 43m
Deal found 11/7![American Airlines logo]()
$472
This American Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/26:44 pm -
2 stops20h 01m
Wed 12/98:15 am -
2 stops13h 25m
Deal found 11/6![American Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 11/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:01 am -
1 stop28h 25m
Thu 12/1012:21 pm -
1 stop10h 27m
Deal found 11/8![American Airlines logo]()
$569
This United Airlines deal was found by Cheapflights users on 11/7. 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.
Tue 12/225:15 am -
2 stops32h 30m
Tue 12/295:10 pm -
2 stops15h 57m
Deal found 11/7![United Airlines logo]()
$619
This American Airlines deal was found by Cheapflights users on 11/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:30 am -
1 stop9h 05m
Wed 12/303:30 pm -
1 stop7h 29m
Deal found 11/8![American Airlines logo]()
$615
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Wed 12/235:15 am -
2 stops34h 45m
Wed 12/305:45 pm -
2 stops25h 18m
Deal found 11/8![United Airlines logo]()
$622
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 November 9, 2026.
Search for one-way flight options from Portland to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated November 9, 2026.
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Sat 2/67:10 am -
2 stops9h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![United Airlines logo]()
$186
This American Airlines deal was found by Cheapflights users on 11/7. 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.
Wed 4/145:10 pm -
2 stops18h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![American Airlines logo]()
$191
This American Airlines deal was found by Cheapflights users on 11/7. 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.
Sun 4/186:01 pm -
2 stops18h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![American Airlines logo]()
$192
This United Airlines deal was found by Cheapflights users on 11/7. 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.
Thu 4/155:45 am -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![United Airlines logo]()
$212
This United Airlines deal was found by Cheapflights users on 11/7. 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.
Sun 4/185:06 pm -
1 stop19h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![United Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 11/7. 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.
Thu 4/156:01 pm -
2 stops18h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![American Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/66:31 pm -
3 stops41h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 11/7. 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.
Fri 4/165:10 pm -
2 stops18h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![American Airlines logo]()
$393
This United Airlines deal was found by Cheapflights users on 11/7. 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 4/165:45 am -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![United Airlines logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 11/7. 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.
Fri 4/1611:10 am -
3 stops29h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Multiple Airlines logo]()
$912
This Kiwi.com deal was found by Cheapflights users on 11/7. 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.
Thu 4/1510:54 am -
3 stops30h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Multiple Airlines logo]()
$951
This Kiwi.com deal was found by Cheapflights users on 11/7. 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.
Sun 4/1810:08 am -
3 stops32h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Multiple Airlines logo]()
$1,070
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 November 9, 2026.
Round-trip from | $472 (American Airlines) |
|---|---|
One-way from | $186 (United Airlines) |
Popular in | April |
Cheapest in | June |
Average price | $684 |
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 November 9, 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
Sat 2/6
7:10 am-4:35 pm
2 stops9h 25m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$186
Quickest round-trip
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Wed 4/14
5:45 am-12:45 pm
1 stop8h 00m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$186
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Thu 4/15
5:45 am-12:45 pm
1 stop8h 00m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$212
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Thu 4/15
6:01 pm-11:32 am
2 stops18h 31m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Fri 4/16
5:45 am-12:45 pm
1 stop8h 00m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$422
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Fri 11/27
6:47 pm-2:40 pm
2 stops19h 53m
George Town Owen Roberts Intl
Fri 12/11
3:45 pm-9:28 am
2 stops17h 43m
$472
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Sat 12/5
7:01 am-11:26 am
1 stop28h 25m
George Town Owen Roberts Intl
Thu 12/10
3:45 pm-9:22 am
2 stops17h 37m
$482
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Sat 5/1
6:00 am-11:00 am
1 stop6h 00m
George Town Owen Roberts Intl
Sat 5/8
4:00 pm-11:15 am
1 stop18h 15m
$560
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Tue 12/22
5:15 am-1:45 pm
2 stops32h 30m
George Town Owen Roberts Intl
Tue 12/29
5:10 pm-9:07 am
2 stops15h 57m
$619
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Wed 12/23
5:15 am-4:00 pm
2 stops34h 45m
George Town Owen Roberts Intl
Wed 12/30
5:45 pm-7:03 pm
2 stops25h 18m
$622
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 November 9, 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
Boarding
8.1
Entertainment
7.8
Crew
8.5
Overall
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Overall
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Overall
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Overall
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
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 November 9, 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 November 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$480 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$200 | Average$565 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$422 | Average$600 | FlexibilityNo cancel fee | On-time71% |