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Cayman Islands

$572+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
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 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$572
(American Airlines)

Popular in

March

Cheapest in

January

Average price

$775
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. 5% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 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 1, 2025.

This American Airlines deal was found by Cheapflights users on 3/31. 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.
Tue 5/65:10 pmBOI - GCM
2 stops17h 00mAmerican Airlines
Fri 5/92:10 pmGCM - BOI
2 stops23h 35mAmerican Airlines
Deal found 3/31$572
This United Airlines deal was found by Cheapflights users on 3/31. 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.
Thu 5/151:35 pmBOI - GCM
2 stops21h 55mUnited Airlines
Thu 5/221:35 pmGCM - BOI
2 stops21h 11mUnited Airlines
Deal found 3/31$606
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1511:59 pmBOI - GCM
1 stop10h 21mDelta
Thu 5/2212:35 pmGCM - BOI
1 stop11h 14mDelta
Deal found 3/31$636
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Sat 5/310:34 pmPDX - GCM
1 stop10h 35mAmerican Airlines
Wed 5/1412:25 pmGCM - PDX
1 stop10h 11mAmerican Airlines
Deal found 3/31$636
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/179:50 pmPDX - GCM
1 stop11h 35mDelta
Mon 6/2312:40 pmGCM - PDX
1 stop13h 12mDelta
Deal found 3/31$671
This Mytrip deal was found by Cheapflights users on 3/31. 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.
Sat 5/32:33 pmPDX - GCM
3 stops28h 47mMultiple Airlines
Wed 5/1411:30 amGCM - PDX
2 stops31h 15mMultiple Airlines
Deal found 3/31$726
This Southwest deal was found by Cheapflights users on 3/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/186:25 pmPDX - GCM
2 stops15h 25mSouthwest
Sun 6/2212:45 pmGCM - PDX
2 stops14h 35mSouthwest
Deal found 3/31$780
This Southwest deal was found by Cheapflights users on 4/1. 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.
Fri 5/236:05 pmBOI - GCM
2 stops17h 10mSouthwest
Sun 6/112:45 pmGCM - BOI
2 stops12h 40mSouthwest
Deal found 4/1$830
This Mytrip deal was found by Cheapflights users on 4/1. 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.
Fri 5/2312:16 pmBOI - GCM
3 stops23h 29mMultiple Airlines
Sun 6/17:00 amGCM - BOI
3 stops29h 21mMultiple Airlines
Deal found 4/1$872
This United Airlines deal was found by Cheapflights users on 3/31. 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 12/2611:25 amPDX - GCM
2 stops26h 25mUnited Airlines
Sun 1/45:40 pmGCM - PDX
2 stops22h 35mUnited Airlines
Deal found 3/31$1,406

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 1, 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

Tue 5/6

5:10 pm-11:10 am

2 stops17h 00m

George Town Owen Roberts Intl

Fri 5/9

2:10 pm-12:45 pm

2 stops23h 35m

$572

BoiseGeorge Town

BOI - GCM

BOIGCM

Boise Air Term. Gowen Fld

Thu 5/15

1:35 pm-12:30 pm

2 stops21h 55m

George Town Owen Roberts Intl

Thu 5/22

1:35 pm-9:46 am

2 stops21h 11m

$606

BoiseGeorge Town

BOI - GCM

BOIGCM

Boise Air Term. Gowen Fld

Thu 5/15

11:59 pm-11:20 am

1 stop10h 21m

George Town Owen Roberts Intl

Thu 5/22

12:35 pm-10:49 pm

1 stop11h 14m

$636

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sat 5/3

10:34 pm-11:09 am

1 stop10h 35m

George Town Owen Roberts Intl

Wed 5/14

12:25 pm-8:36 pm

1 stop10h 11m

$636

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 6/17

9:50 pm-11:25 am

1 stop11h 35m

George Town Owen Roberts Intl

Mon 6/23

12:40 pm-11:52 pm

1 stop13h 12m

$671

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sat 5/3

2:33 pm-9:20 pm

3 stops28h 47m

George Town Owen Roberts Intl

Wed 5/14

11:30 am-4:45 pm

2 stops31h 15m

$726

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 6/18

6:25 pm-11:50 am

2 stops15h 25m

George Town Owen Roberts Intl

Sun 6/22

12:45 pm-1:20 am

2 stops14h 35m

$780

BoiseGeorge Town

BOI - GCM

BOIGCM

Boise Air Term. Gowen Fld

Fri 5/23

6:05 pm-12:15 pm

2 stops17h 10m

George Town Owen Roberts Intl

Sun 6/1

12:45 pm-12:25 am

2 stops12h 40m

$830

BoiseGeorge Town

BOI - GCM

BOIGCM

Boise Air Term. Gowen Fld

Fri 5/23

12:16 pm-12:45 pm

3 stops23h 29m

George Town Owen Roberts Intl

Sun 6/1

7:00 am-11:21 am

3 stops29h 21m

$872

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 4/28

1:45 pm-12:30 pm

3 stops20h 45m

George Town Owen Roberts Intl

Mon 5/5

1:35 pm-1:12 pm

2 stops25h 37m

$1,555

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 April 1, 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 1, 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
4,277 reviews

Entertainment

7.6

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,277 reviews
Southwest
8.0
Very good
4,277 reviews

Entertainment

7.6

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,277 reviews

Entertainment

7.6

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,615 reviews
Southwest
8.0
Very good
4,277 reviews

Entertainment

7.6

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,277 reviews

Entertainment

7.6

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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

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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 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$506Average$624FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$516Average$776FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$576Average$775FlexibilityNo cancel feeOn-time69%

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