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Cayman Islands

$265+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$458
(Delta)

One-way from

$265
(Mytrip)

Popular in

September

Cheapest in

January

Average price

$663
From Oregon to Cayman Islands
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One-way flight from Oregon to Cayman Islands
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Highest demand for flights based on searches. 6% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Delta deal was found by Cheapflights users on 7/30. 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.
Mon 11/1711:23 amMFR - GCM
2 stops22h 14mDelta
Fri 11/212:02 pmGCM - MFR
2 stops23h 53mDelta
Deal found 7/30$458
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 9/241:00 pmBOI - GCM
2 stops21h 36mDelta
Sun 10/512:52 pmGCM - BOI
1 stop10h 31mDelta
Deal found 7/29$548
This American Airlines deal was found by Cheapflights users on 7/30. 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 9/276:00 amEUG - GCM
2 stops27h 22mAmerican Airlines
Wed 10/112:25 pmGCM - EUG
2 stops37h 04mAmerican Airlines
Deal found 7/30$581
This Mytrip deal was found by Cheapflights users on 7/31. 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.
Sun 9/1410:00 amPDX - GCM
2 stops23h 55mMultiple Airlines
Sun 9/217:00 amGCM - PDX
2 stops30h 11mMultiple Airlines
Deal found 7/31$603
This United Airlines deal was found by Cheapflights users on 7/31. 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 8/293:44 pmPDX - GCM
2 stops18h 46mUnited Airlines
Sat 9/61:35 pmGCM - PDX
1 stop10h 48mUnited Airlines
Deal found 7/31$666
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Wed 9/241:07 pmBOI - GCM
2 stops21h 03mAmerican Airlines
Sun 10/512:10 pmGCM - BOI
2 stops25h 33mAmerican Airlines
Deal found 7/30$668
This American Airlines deal was found by Cheapflights users on 7/31. 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 10/139:52 pmPDX - GCM
2 stops13h 18mAmerican Airlines
Fri 10/178:25 amGCM - PDX
2 stops14h 37mAmerican Airlines
Deal found 7/31$670
This United Airlines deal was found by Cheapflights users on 7/30. 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 7/312:12 pmMFR - GCM
2 stops20h 18mUnited Airlines
Thu 8/71:35 pmGCM - MFR
2 stops24h 17mUnited Airlines
Deal found 7/30$888
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Thu 7/319:51 pmMFR - GCM
3 stops16h 14mMultiple Airlines
Thu 8/74:45 pmGCM - MFR
2 stops23h 55mMultiple Airlines
Deal found 7/30$1,055
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Sat 11/2212:48 pmBOI - GCM
2 stops21h 32mMultiple Airlines
Sat 11/2911:25 amGCM - BOI
3 stops29h 04mMultiple Airlines
Deal found 7/30$1,152
This Southwest deal was found by Cheapflights users on 7/30. 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.
Sat 11/226:50 pmBOI - GCM
2 stops15h 45mSouthwest
Sat 11/292:20 pmGCM - BOI
2 stops21h 25mSouthwest
Deal found 7/30$1,370

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 July 31, 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

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Mon 11/17

11:23 am-12:37 pm

2 stops22h 14m

George Town Owen Roberts Intl

Fri 11/21

2:02 pm-10:55 am

2 stops23h 53m

$458

BoiseGeorge Town

BOI - GCM

BOIGCM

Boise Air Term. Gowen Fld

Wed 9/24

1:00 pm-11:36 am

2 stops21h 36m

George Town Owen Roberts Intl

Sun 10/5

12:52 pm-10:23 pm

1 stop10h 31m

$548

EugeneGeorge Town

EUG - GCM

EUGGCM

Eugene

Sat 9/27

6:00 am-11:22 am

2 stops27h 22m

George Town Owen Roberts Intl

Wed 10/1

12:25 pm-11:29 pm

2 stops37h 04m

$581

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 9/14

10:00 am-11:55 am

2 stops23h 55m

George Town Owen Roberts Intl

Sun 9/21

7:00 am-11:11 am

2 stops30h 11m

$603

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 8/29

3:44 pm-12:30 pm

2 stops18h 46m

George Town Owen Roberts Intl

Sat 9/6

1:35 pm-10:23 pm

1 stop10h 48m

$666

BoiseGeorge Town

BOI - GCM

BOIGCM

Boise Air Term. Gowen Fld

Wed 9/24

1:57 pm-11:10 am

2 stops20h 13m

George Town Owen Roberts Intl

Sun 10/5

12:10 pm-12:43 pm

2 stops25h 33m

$668

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 10/13

9:52 pm-1:10 pm

2 stops13h 18m

George Town Owen Roberts Intl

Fri 10/17

8:25 am-9:02 pm

2 stops14h 37m

$670

BoiseGeorge Town

BOI - GCM

BOIGCM

Boise Air Term. Gowen Fld

Fri 9/12

9:16 pm-4:05 pm

2 stops17h 49m

George Town Owen Roberts Intl

Fri 9/19

7:00 am-1:21 pm

3 stops31h 21m

$1,219

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 9/22

12:07 pm-4:10 pm

3 stops26h 03m

$265

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 9/22

9:56 pm-11:10 am

2 stops11h 14m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 11 results
1
2

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 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.

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 July 31, 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 July 31, 2025.
Read through reviews of airlines operating flights from Oregon to the Cayman Islands, such as Delta, United Airlines, and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,978 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Oregon to Cayman Islands

Discover the top 2 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$516Average$923FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$576Average$838FlexibilityNo cancel feeOn-time69%

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