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Cayman Islands

$636+ Cheap flights from Oregon 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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheap flight deals from Oregon to Cayman Islands

Keep the following information in mind while searching for Oregon to Cayman Islands flight deals. Data was last updated April 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$636
(United Airlines)

Popular in

April

Cheapest in

January

Average price

$832
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 Oregon to Cayman Islands
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Highest demand for flights based on searches. 9% potential increase in price ($70 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Oregon to Cayman Islands

Cheapest flights from Oregon to Cayman Islands
Explore the most affordable flight options available from Oregon to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This United Airlines deal was found by Cheapflights users on 4/23. 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 8/92:02 pmEUG - GCM
2 stops20h 28mUnited Airlines
Sat 8/161:35 pmGCM - EUG
2 stops11h 06mUnited Airlines
Deal found 4/23$636
This Southwest deal was found by Cheapflights users on 4/24. 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.
Wed 7/29:15 pmPDX - GCM
2 stops12h 35mSouthwest
Mon 7/712:45 pmGCM - PDX
2 stops13h 20mSouthwest
Deal found 4/24$665
This Delta deal was found by Cheapflights users on 4/23. 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 8/225:10 pmPDX - GCM
2 stops16h 21mDelta
Sun 8/3112:50 pmGCM - PDX
2 stops13h 02mDelta
Deal found 4/23$695
This American Airlines deal was found by Cheapflights users on 4/23. 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 8/93:51 pmEUG - GCM
2 stops18h 59mAmerican Airlines
Sat 8/1612:30 pmGCM - EUG
1 stop10h 18mAmerican Airlines
Deal found 4/23$725
This Mytrip deal was found by Cheapflights users on 4/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/201:37 pmPDX - GCM
2 stops24h 33mMultiple Airlines
Tue 5/2711:30 amGCM - PDX
2 stops27h 12mMultiple Airlines
Deal found 4/22$727
This United Airlines deal was found by Cheapflights users on 4/24. 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 7/21:37 pmPDX - GCM
2 stops20h 53mUnited Airlines
Mon 7/71:35 pmGCM - PDX
1 stop10h 58mUnited Airlines
Deal found 4/24$736
This American Airlines deal was found by Cheapflights users on 4/24. 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.
Tue 7/112:09 amPDX - GCM
2 stops11h 01mAmerican Airlines
Mon 7/73:30 pmGCM - PDX
1 stop9h 29mAmerican Airlines
Deal found 4/24$779
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 8/97:32 pmEUG - GCM
1 stop17h 58mMultiple Airlines
Sat 8/164:00 pmGCM - EUG
1 stop20h 17mMultiple Airlines
Deal found 4/23$901
This American Airlines deal was found by Cheapflights users on 4/23. 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 12/213:29 pmMFR - GCM
2 stops20h 00mAmerican Airlines
Sun 1/44:40 pmGCM - MFR
2 stops23h 14mAmerican Airlines
Deal found 4/23$1,117
This United Airlines deal was found by Cheapflights users on 4/23. 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 12/212:05 pmMFR - GCM
3 stops23h 20mUnited Airlines
Sun 1/45:40 pmGCM - MFR
2 stops21h 30mUnited Airlines
Deal found 4/23$3,876

Cheapflights Fare Finder

Customize your flight search to find flights from Oregon 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 April 24, 2025.
Use the filters below to find and compare flights from Oregon to the Cayman Islands that are best for you.

Fly from

Oregon

Fly to

Cayman Islands

Route

Depart

Return

Price

EugeneGeorge Town

EUG - GCM

EUGGCM

Eugene

Sat 8/9

2:02 pm-12:30 pm

2 stops20h 28m

George Town Owen Roberts Intl

Sat 8/16

1:35 pm-10:41 pm

2 stops11h 06m

$636

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 7/2

9:15 pm-11:50 am

2 stops12h 35m

George Town Owen Roberts Intl

Mon 7/7

12:45 pm-12:05 am

2 stops13h 20m

$665

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 8/22

5:10 pm-11:31 am

2 stops16h 21m

George Town Owen Roberts Intl

Sun 8/31

12:50 pm-11:52 pm

2 stops13h 02m

$695

EugeneGeorge Town

EUG - GCM

EUGGCM

Eugene

Sat 8/9

3:51 pm-12:50 pm

2 stops18h 59m

George Town Owen Roberts Intl

Sat 8/16

12:30 pm-8:48 pm

1 stop10h 18m

$725

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 5/20

1:37 pm-4:10 pm

2 stops24h 33m

George Town Owen Roberts Intl

Tue 5/27

11:30 am-12:42 pm

2 stops27h 12m

$727

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 7/2

1:37 pm-12:30 pm

2 stops20h 53m

George Town Owen Roberts Intl

Mon 7/7

1:35 pm-10:33 pm

1 stop10h 58m

$736

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 7/1

12:09 am-1:10 pm

2 stops11h 01m

George Town Owen Roberts Intl

Mon 7/7

3:30 pm-10:59 pm

1 stop9h 29m

$779

EugeneGeorge Town

EUG - GCM

EUGGCM

Eugene

Sat 8/9

7:32 pm-3:30 pm

1 stop17h 58m

George Town Owen Roberts Intl

Sat 8/16

4:00 pm-10:17 am

1 stop20h 17m

$901

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Best time to book a flight from Oregon to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Oregon 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 Oregon to the Cayman Islands

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

Find hourly flight availability from Oregon 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 April 24, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Cayman Islands as you normally would.

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 April 24, 2025.
Read through reviews of airlines operating flights from Oregon to Cayman Islands, such as Southwest, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,685 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Oregon to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oregon 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 Oregon to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Oregon to Cayman Islands (average of $467). Flying from Oregon to Cayman Islands in March is currently the most expensive (average of $594). 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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Top 3 airlines flying from Oregon to Cayman Islands

Discover the top 3 airlines that operate flights from Oregon 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$506Average$624FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$516Average$772FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$576Average$775FlexibilityNo cancel feeOn-time69%

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