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Cayman Islands

$281+ Cheap flights from Portland (PDX) 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
dic. 24 — dic. 311
mié. 12/24
mié. 12/31
1 adult, Economy
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Find flight deals from Portland to Cayman Islands

Cheapest flights from Portland to Cayman Islands
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 noviembre 24, 2025.

This American Airlines deal was found by Cheapflights users on 11/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/2211:59 pmPDX - GCM
1 stop12h 26mAmerican Airlines
mar. 12/301:05 pmGCM - PDX
1 stop14h 54mAmerican Airlines
Deal found 11/22$691
This United Airlines deal was found by Cheapflights users on 11/22. 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.
lun. 12/2211:55 pmPDX - GCM
1 stop10h 50mUnited Airlines
mar. 12/305:45 pmGCM - PDX
2 stops19h 16mUnited Airlines
Deal found 11/22$701
This Kiwi.com deal was found by Cheapflights users on 11/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/57:44 pmPDX - GCM
2 stops18h 11mMultiple Airlines
mié. 12/1011:30 amGCM - PDX
1 stop12h 20mMultiple Airlines
Deal found 11/22$765
This Southwest deal was found by Cheapflights users on 11/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/56:55 pmPDX - GCM
2 stops15h 05mSouthwest
mié. 12/101:30 pmGCM - PDX
2 stops12h 05mSouthwest
Deal found 11/22$791
This Delta deal was found by Cheapflights users on 11/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/510:10 pmPDX - GCM
1 stop11h 20mDelta
mié. 12/101:50 pmGCM - PDX
1 stop11h 29mDelta
Deal found 11/22$796
This United Airlines deal was found by Cheapflights users on 11/22. 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.
vie. 12/511:59 pmPDX - GCM
2 stops13h 21mUnited Airlines
mié. 12/105:45 pmGCM - PDX
3 stops20h 18mUnited Airlines
Deal found 11/22$801
This United Airlines deal was found by Cheapflights users on 11/22. 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.
mié. 11/263:54 pmPDX - GCM
2 stops21h 36mUnited Airlines
vie. 11/285:45 pmGCM - PDX
2 stops18h 53mUnited Airlines
Deal found 11/22$845

Cheap 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 noviembre 24, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$642
(Kiwi.com)

One-way from

$281
(American Airlines)

Popular in

March

Cheapest in

January

Average price

$816
Provider with most accurate pricing for Portland-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Portland-George Town Owen Roberts Intl flights.
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From Portland to Cayman Islands
Search Deals
One-way flight from Portland to Cayman Islands
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Highest demand for flights based on searches. 12% potential increase in price ($113 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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 noviembre 24, 2025.
Use the filters below to find and compare flights from Portland to the Cayman Islands that are best for you.

Fly from

Portland

Fly to

Cayman Islands

Route

Depart

Return

Price

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

lun. 1/12

7:00 am-9:15 pm

1 stop11h 15m

George Town Owen Roberts Intl

mié. 1/14

11:30 am-9:29 am

2 stops24h 59m

$642

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

jue. 1/15

11:59 pm-1:45 pm

1 stop10h 46m

George Town Owen Roberts Intl

lun. 1/19

2:50 pm-10:32 pm

1 stop10h 42m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

vie. 1/23

9:45 pm-12:40 pm

1 stop11h 55m

George Town Owen Roberts Intl

sáb. 1/31

2:05 pm-10:15 pm

1 stop11h 10m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

lun. 4/20

10:38 pm-12:45 pm

2 stops12h 07m

George Town Owen Roberts Intl

sáb. 4/25

3:15 pm-10:09 am

2 stops20h 54m

$671

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

mié. 1/28

10:15 pm-2:45 pm

2 stops13h 30m

$281

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

mié. 1/28

7:45 am-1:45 pm

3 stops27h 00m

$336

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

mar. 1/27

6:00 am-8:20 pm

2 stops11h 20m

$760

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/22

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.
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

What is the cheapest month to book a flight from Portland to Cayman Islands?

Currently, December is the cheapest month in which you can book a flight from Portland to Cayman Islands (average of $434). Flying from Portland to Cayman Islands in February is currently the most expensive (average of $784). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PDX to KY?

Find hourly flight availability from Portland to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated noviembre 24, 2025.

One of the essential ways to save on airfare from Portland to Cayman Islands is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 33% on airfare.

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 noviembre 24, 2025.
Read reviews from past customers who have flown United Airlines and American Airlines from Portland to the Cayman Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,044 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,044 reviews
United Airlines
7.4
Good
9,044 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,040 reviews
United Airlines
7.4
Good
9,044 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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.

  • What airport do you fly from for flights from Portland to Cayman Islands?

    Portland (PDX), located 6.0 mi from the city center, is the airport you fly out of when you book flights from Portland to Cayman Islands.

  • How long is the flight from Portland to Cayman Islands?

    Airlines like United Airlines and Delta fly from Portland to Cayman Islands in about 10h 46m. The time it takes to get you to your destination can typically vary by up to 1h 09m. The distance between Portland and Cayman Islands is about 2961 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Portland to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Portland to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Cayman Islands.

  • Can I find deals for business class flights from Portland to Cayman Islands?

    Yes. Cheapflights offers flight deals from Portland to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland to Cayman Islands?

    Currently, December is the cheapest month in which you can book a flight from Portland to Cayman Islands (average of $434). Flying from Portland to Cayman Islands in February is currently the most expensive (average of $784). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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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.
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Top 2 airlines flying from Portland to Cayman Islands

Discover the top 2 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 noviembre 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$578Average$838FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$608Average$799FlexibilityNo cancel feeOn-time71%

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