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Cayman Islands

$232+ 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Cheap 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 December 8, 2025.

This Booking.com deal was found by Cheapflights users on 12/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:00 pmPDX - GCM
2 stops38h 25mAir Canada
Thu 12/111:30 pmGCM - PDX
2 stops32h 00mAir Canada
Deal found 12/5$769
This Southwest deal was found by Cheapflights users on 12/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:55 pmPDX - GCM
2 stops14h 40mSouthwest
Wed 12/241:30 pmGCM - PDX
2 stops12h 05mSouthwest
Deal found 12/7$791
This American Airlines deal was found by Cheapflights users on 12/7. 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.
Mon 12/1510:45 pmPDX - GCM
1 stop12h 59mAmerican Airlines
Wed 12/241:05 pmGCM - PDX
1 stop14h 54mAmerican Airlines
Deal found 12/7$796
This Orbitz deal was found by Cheapflights users on 12/7. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/157:00 pmPDX - GCM
2 stops14h 25mMultiple Airlines
Wed 12/247:00 amGCM - PDX
1 stop16h 50mMultiple Airlines
Deal found 12/7$799
This American Airlines deal was found by Cheapflights users on 12/6. 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.
Sun 12/2110:21 pmPDX - GCM
1 stop10h 36mAmerican Airlines
Sat 12/273:45 pmGCM - PDX
1 stop12h 14mAmerican Airlines
Deal found 12/6$836
This Delta deal was found by Cheapflights users on 12/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/710:10 pmPDX - GCM
1 stop11h 25mDelta
Thu 12/111:50 pmGCM - PDX
1 stop11h 29mDelta
Deal found 12/5$840
This United Airlines deal was found by Cheapflights users on 12/7. 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.
Mon 12/1511:59 pmPDX - GCM
2 stops13h 31mUnited Airlines
Wed 12/245:10 pmGCM - PDX
3 stops28h 38mUnited Airlines
Deal found 12/7$911

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 December 8, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$519
(Southwest)

One-way from

$232
(Kiwi.com)

Popular in

March

Cheapest in

July

Average price

$1,077
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.
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From Portland to Cayman Islands
Search Deals
One-way flight from Portland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($115 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 8, 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 2/23

4:15 pm-12:55 pm

2 stops17h 40m

George Town Owen Roberts Intl

Thu 2/26

1:50 pm-12:45 am

2 stops13h 55m

$519

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 2/23

7:00 am-4:05 pm

1 stop30h 05m

George Town Owen Roberts Intl

Thu 2/26

2:40 pm-11:44 pm

2 stops12h 04m

$521

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 1/12

9:50 am-12:25 pm

2 stops23h 35m

George Town Owen Roberts Intl

Thu 1/15

1:30 pm-6:30 pm

2 stops32h 00m

$579

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 1/5

7:00 am-9:15 pm

1 stop11h 15m

George Town Owen Roberts Intl

Mon 1/12

4:45 pm-12:09 am

2 stops34h 24m

$594

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 3/17

7:00 am-4:05 pm

1 stop31h 05m

George Town Owen Roberts Intl

Sun 3/22

4:45 pm-8:30 pm

1 stop29h 45m

$617

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 1/8

7:00 am-9:15 pm

1 stop11h 15m

George Town Owen Roberts Intl

Thu 1/22

7:00 am-8:27 pm

1 stop16h 27m

$623

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 1/23

9:45 pm-10:57 am

1 stop10h 12m

George Town Owen Roberts Intl

Sat 1/31

3:25 pm-10:15 pm

1 stop9h 50m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 3/17

3:45 pm-3:30 pm

2 stops21h 45m

George Town Owen Roberts Intl

Sun 3/22

1:50 pm-10:45 pm

1 stop10h 55m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 6/1

6:46 pm-10:55 am

2 stops14h 09m

George Town Owen Roberts Intl

Mon 6/15

3:15 pm-9:07 am

2 stops19h 52m

$671

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 3/25

7:00 am-11:35 am

1 stop26h 35m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

Showing 1-10 of 17 results
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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 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 December 8, 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 December 8, 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
9,089 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,089 reviews
United Airlines
7.4
Good
9,089 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
American Airlines
7.2
Good
11,045 reviews
United Airlines
7.4
Good
9,089 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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 and Air Canada fly from Portland to Cayman Islands in about 17h 40m. The time it takes to get you to your destination can typically vary by up to 5h 55m. 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.

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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Boise to Castries flights
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Portland to Puerto Plata flights
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Portland to Rock Sound flights
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Redmond to Saint Thomas Island flights
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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 December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$578Average$838FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$609Average$803FlexibilityNo cancel feeOn-time71%

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