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Cayman Islands

$245+ Cheap flights from Oregon 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
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Oregon to Cayman Islands

Best flights from Oregon to Cayman Islands
Discover carefully curated flight deals from Oregon to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/14. 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 2/237:02 pmBOI - GCM
2 stops15h 03mAmerican Airlines
Sun 3/13:45 pmGCM - BOI
2 stops21h 16mAmerican Airlines
Deal found 12/14$474
This Southwest deal was found by Cheapflights users on 12/17. 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 2/233:40 pmPDX - GCM
2 stops18h 15mSouthwest
Thu 2/261:50 pmGCM - PDX
2 stops13h 15mSouthwest
Deal found 12/17$494
This Orbitz deal was found by Cheapflights users on 12/18. 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 1/267:00 pmPDX - GCM
2 stops14h 25mAir Canada
Mon 2/21:30 pmGCM - PDX
2 stops28h 10mAir Canada
Deal found 12/18$525
This Orbitz deal was found by Cheapflights users on 12/18. 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 1/267:00 amPDX - GCM
1 stop30h 05mMultiple Airlines
Mon 2/24:45 pmGCM - PDX
1 stop30h 42mMultiple Airlines
Deal found 12/18$577
This United Airlines deal was found by Cheapflights users on 12/14. 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 1/262:09 pmEUG - GCM
2 stops20h 06mUnited Airlines
Thu 1/292:50 pmGCM - EUG
2 stops49h 17mUnited Airlines
Deal found 12/14$597
This Air Canada deal was found by Cheapflights users on 12/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/117:00 pmPDX - GCM
2 stops38h 25mAir Canada
Thu 1/151:30 pmGCM - PDX
2 stops46h 45mAir Canada
Deal found 12/17$559
This Travelocity deal was found by Cheapflights users on 12/17. 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.
Mon 2/237:05 pmPDX - GCM
2 stops14h 20mMultiple Airlines
Thu 2/267:00 amGCM - PDX
1 stop16h 44mMultiple Airlines
Deal found 12/17$585
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/32:08 pmEUG - GCM
2 stops20h 07mUnited Airlines
Thu 3/52:50 pmGCM - EUG
2 stops49h 17mUnited Airlines
Deal found 12/15$597
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/262:00 pmMFR - GCM
2 stops20h 15mUnited Airlines
Thu 1/292:50 pmGCM - MFR
2 stops33h 12mUnited Airlines
Deal found 12/15$597
This American Airlines deal was found by Cheapflights users on 12/16. 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 1/2311:01 pmPDX - GCM
1 stop9h 49mAmerican Airlines
Sat 1/313:45 pmGCM - PDX
1 stop11h 01mAmerican Airlines
Deal found 12/16$666
This United Airlines deal was found by Cheapflights users on 12/16. 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 1/105:00 amMFR - GCM
2 stops29h 45mUnited Airlines
Tue 1/132:25 pmGCM - MFR
2 stops33h 37mUnited Airlines
Deal found 12/16$598
This United Airlines deal was found by Cheapflights users on 12/16. 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 1/1811:05 pmPDX - GCM
1 stop11h 10mUnited Airlines
Sun 1/252:50 pmGCM - PDX
1 stop10h 42mUnited Airlines
Deal found 12/16$666
This United Airlines deal was found by Cheapflights users on 12/17. 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 2/2110:38 pmPDX - GCM
1 stop11h 37mUnited Airlines
Sat 2/285:30 pmGCM - PDX
2 stops21h 25mUnited Airlines
Deal found 12/17$671
This American Airlines deal was found by Cheapflights users on 12/16. 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 3/147:20 pmBOI - GCM
2 stops17h 05mAmerican Airlines
Sun 3/222:36 pmGCM - BOI
1 stop23h 25mAmerican Airlines
Deal found 12/16$1,438
This United Airlines deal was found by Cheapflights users on 12/16. 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 3/145:30 pmBOI - GCM
2 stops17h 45mUnited Airlines
Sun 3/224:45 pmGCM - BOI
2 stops44h 28mUnited Airlines
Deal found 12/16$1,140

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$474
(American Airlines)

One-way from

$245
(Air Canada)

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.
Search Deals
From Oregon to Cayman Islands
Search Deals
One-way flight from Oregon 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 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 December 18, 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

BoiseGeorge Town

BOI - GCM

BOIGCM

Boise Air Term. Gowen Fld

Mon 2/23

7:02 pm-12:05 pm

2 stops15h 03m

George Town Owen Roberts Intl

Sun 3/1

3:45 pm-11:01 am

2 stops21h 16m

$474

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 2/23

3:40 pm-12:55 pm

2 stops18h 15m

George Town Owen Roberts Intl

Thu 2/26

1:50 pm-12:05 am

2 stops13h 15m

$494

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 1/26

7:00 pm-12:25 pm

2 stops14h 25m

George Town Owen Roberts Intl

Mon 2/2

1:30 pm-2:40 pm

2 stops28h 10m

$525

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 1/11

7:00 pm-12:25 pm

2 stops38h 25m

George Town Owen Roberts Intl

Thu 1/15

1:30 pm-9:15 am

2 stops46h 45m

$559

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 1/26

7:00 am-4:05 pm

1 stop30h 05m

George Town Owen Roberts Intl

Mon 2/2

4:45 pm-8:27 pm

1 stop30h 42m

$577

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 2/23

7:05 pm-12:25 pm

2 stops14h 20m

George Town Owen Roberts Intl

Thu 2/26

7:00 am-8:44 pm

1 stop16h 44m

$585

EugeneGeorge Town

EUG - GCM

EUGGCM

Eugene

Mon 1/26

2:09 pm-1:15 pm

2 stops20h 06m

George Town Owen Roberts Intl

Thu 1/29

2:50 pm-1:07 pm

2 stops49h 17m

$597

EugeneGeorge Town

EUG - GCM

EUGGCM

Eugene

Tue 3/3

2:08 pm-1:15 pm

2 stops20h 07m

George Town Owen Roberts Intl

Thu 3/5

2:50 pm-1:07 pm

2 stops49h 17m

$597

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Mon 1/26

2:00 pm-1:15 pm

2 stops20h 15m

George Town Owen Roberts Intl

Thu 1/29

2:50 pm-9:02 pm

2 stops33h 12m

$597

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Sat 1/10

5:00 am-1:45 pm

2 stops29h 45m

George Town Owen Roberts Intl

Tue 1/13

2:25 pm-9:02 pm

2 stops33h 37m

$598

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 21 results
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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 December 18, 2025.

One of the essential ways to save on airfare from Oregon 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 evening could potentially save you up to 19% on airfare.

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.

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

    American Airlines, Southwest, and Air Canada can get you from Oregon to Cayman Islands in just under 14h 25m. Your travel time can differ by up to 3h 50m. Airlines will cover a distance of 2961 mi. This flight may include one or multiple stops.

  • 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Oregon to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Oregon to Cayman Islands

Discover the top airline 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$609Average$942FlexibilityNo cancel feeOn-time71%

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