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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
Dec 16 — Dec 231
Tue 12/16
Tue 12/23
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 November 16, 2025.

This Expedia deal was found by Cheapflights users on 11/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:00 pmPDX - GCM
2 stops14h 25mMultiple Airlines
Wed 12/1011:30 amGCM - PDX
1 stop12h 20mMultiple Airlines
Deal found 11/15$660
This United Airlines deal was found by Cheapflights users on 11/13. 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 12/1211:59 pmPDX - GCM
2 stops13h 36mUnited Airlines
Fri 12/192:50 pmGCM - PDX
1 stop10h 50mUnited Airlines
Deal found 11/13$666
This Delta deal was found by Cheapflights users on 11/13. 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 12/125:30 pmPDX - GCM
2 stops16h 00mDelta
Fri 12/191:50 pmGCM - PDX
2 stops13h 25mDelta
Deal found 11/13$671
This American Airlines deal was found by Cheapflights users on 11/15. 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 12/2912:49 amPDX - GCM
1 stop11h 36mAmerican Airlines
Tue 1/68:45 amGCM - PDX
2 stops14h 42mAmerican Airlines
Deal found 11/15$710
This American Airlines deal was found by Cheapflights users on 11/15. 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 12/410:15 pmPDX - GCM
1 stop12h 51mAmerican Airlines
Wed 12/101:05 pmGCM - PDX
1 stop10h 12mAmerican Airlines
Deal found 11/15$711
This Delta deal was found by Cheapflights users on 11/15. 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 12/510:10 pmPDX - GCM
1 stop11h 20mDelta
Wed 12/101:50 pmGCM - PDX
2 stops13h 25mDelta
Deal found 11/15$716
This United Airlines deal was found by Cheapflights users on 11/13. 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 12/259:00 amPDX - GCM
2 stops28h 00mUnited Airlines
Wed 1/72:25 pmGCM - PDX
2 stops22h 20mUnited Airlines
Deal found 11/13$781
This United Airlines deal was found by Cheapflights users on 11/13. 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 12/2911:55 pmPDX - GCM
1 stop10h 50mUnited Airlines
Mon 1/55:10 pmGCM - PDX
2 stops23h 35mUnited Airlines
Deal found 11/13$793
This American Airlines deal was found by Cheapflights users on 11/13. 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 12/255:33 amPDX - GCM
2 stops11h 45mAmerican Airlines
Wed 1/78:45 amGCM - PDX
1 stop18h 01mAmerican Airlines
Deal found 11/13$811
This Travelocity deal was found by Cheapflights users on 11/13. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:00 amPDX - GCM
1 stop11h 15mMultiple Airlines
Wed 1/75:10 pmGCM - PDX
1 stop30h 33mMultiple Airlines
Deal found 11/13$847

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 November 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$495
(Southwest)

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.
Search Deals
Provider most trusted by Cheapflights users for Portland-George Town Owen Roberts Intl flights.
Search Deals
From Portland to Cayman Islands
Search Deals
One-way flight from Portland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($135 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 16, 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

Mon 3/2

3:40 pm-12:55 pm

2 stops18h 15m

George Town Owen Roberts Intl

Thu 3/5

1:35 pm-12:45 am

2 stops14h 10m

$495

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 3/4

2:15 pm-12:40 pm

2 stops19h 25m

George Town Owen Roberts Intl

Sun 3/8

12:55 pm-1:30 am

2 stops14h 35m

$578

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 3/2

7:00 pm-12:25 pm

2 stops14h 25m

George Town Owen Roberts Intl

Thu 3/5

7:00 am-8:44 pm

1 stop16h 44m

$632

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 3/2

7:00 pm-12:25 pm

2 stops14h 25m

George Town Owen Roberts Intl

Fri 3/6

7:00 am-8:44 pm

1 stop16h 44m

$651

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 12/4

7:00 pm-12:25 pm

2 stops14h 25m

George Town Owen Roberts Intl

Wed 12/10

11:30 am-8:50 pm

1 stop12h 20m

$660

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 3/17

3:10 pm-11:40 am

2 stops18h 30m

George Town Owen Roberts Intl

Mon 3/23

12:35 pm-12:45 am

2 stops14h 10m

$661

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 3/5

2:30 pm-12:40 pm

2 stops19h 10m

George Town Owen Roberts Intl

Sun 3/8

12:55 pm-1:00 am

2 stops14h 05m

$661

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 3/5

7:00 am-9:15 pm

1 stop11h 15m

George Town Owen Roberts Intl

Sun 3/8

8:00 am-8:33 pm

1 stop14h 33m

$663

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 12/29

12:49 am-3:25 pm

1 stop11h 36m

George Town Owen Roberts Intl

Tue 1/6

1:05 pm-11:46 pm

1 stop13h 41m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 3/17

9:45 pm-11:35 am

1 stop11h 50m

George Town Owen Roberts Intl

Mon 3/23

1:00 pm-10:39 pm

1 stop11h 39m

$666

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 14 results
1
2

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 August is currently the most expensive (average of $801). 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 November 16, 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 November 16, 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
9,017 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

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
9,017 reviews
United Airlines
7.4
Good
9,017 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

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
11,051 reviews
United Airlines
7.4
Good
9,017 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

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 Southwest fly from Portland to Cayman Islands in about 18h 15m. The time it takes to get you to your destination can typically vary by up to . The distance between Portland and Cayman Islands is about 2961 mi.

  • 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 August is currently the most expensive (average of $801). 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 November 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$578Average$838FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$608Average$799FlexibilityNo cancel feeOn-time71%

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