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Cayman Islands

$518+ Cheap flights from Portland (PDX) 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap 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 September 17, 2025.

Round-trip from

$518
(Southwest)

Popular in

February

Cheapest in

January

Average price

$749
From Portland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find 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 September 17, 2025.

This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/167:10 pmPDX - GCM
2 stops14h 25mSouthwest
Wed 11/191:30 pmGCM - PDX
2 stops12h 05mSouthwest
Deal found 9/16$518
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/812:55 pmPDX - GCM
2 stops20h 40mSouthwest
Tue 11/111:30 pmGCM - PDX
2 stops12h 00mSouthwest
Deal found 9/16$593
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:00 pmPDX - GCM
2 stops39h 25mAir Canada
Fri 11/71:30 pmGCM - PDX
2 stops22h 45mAir Canada
Deal found 9/16$650
This Southwest deal was found by Cheapflights users on 9/17. 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.
Wed 11/197:15 pmPDX - GCM
2 stops14h 20mSouthwest
Wed 11/261:30 pmGCM - PDX
2 stops13h 55mSouthwest
Deal found 9/17$665
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/810:10 pmPDX - GCM
1 stop11h 25mDelta
Mon 11/101:50 pmGCM - PDX
1 stop11h 31mDelta
Deal found 9/16$666
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/85:25 pmPDX - GCM
2 stops16h 10mDelta
Wed 11/121:50 pmGCM - PDX
2 stops11h 51mDelta
Deal found 9/16$670
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/29:56 pmPDX - GCM
1 stop11h 29mAmerican Airlines
Tue 10/712:25 pmGCM - PDX
1 stop9h 52mAmerican Airlines
Deal found 9/15$711
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/97:22 pmPDX - GCM
2 stops14h 13mDelta
Tue 11/111:50 pmGCM - PDX
2 stops22h 14mDelta
Deal found 9/16$742
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/99:52 pmPDX - GCM
1 stop11h 33mAmerican Airlines
Tue 10/1412:25 pmGCM - PDX
1 stop9h 52mAmerican Airlines
Deal found 9/16$751

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 September 17, 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

Sat 11/8

12:55 pm-12:35 pm

2 stops20h 40m

George Town Owen Roberts Intl

Tue 11/11

1:30 pm-10:30 pm

2 stops12h 00m

$593

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 1/1

7:00 am-9:15 pm

1 stop11h 15m

George Town Owen Roberts Intl

Tue 1/13

11:30 am-8:23 pm

1 stop11h 53m

$614

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 10/31

7:00 pm-12:25 pm

2 stops39h 25m

George Town Owen Roberts Intl

Fri 11/7

1:30 pm-9:15 am

2 stops22h 45m

$650

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 11/19

7:15 pm-12:35 pm

2 stops14h 20m

George Town Owen Roberts Intl

Wed 11/26

1:30 pm-12:25 am

2 stops13h 55m

$665

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sat 11/8

10:10 pm-12:35 pm

1 stop11h 25m

George Town Owen Roberts Intl

Mon 11/10

1:50 pm-10:21 pm

1 stop11h 31m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 11/19

10:15 pm-11:57 am

1 stop10h 42m

George Town Owen Roberts Intl

Wed 11/26

3:36 pm-11:31 pm

1 stop10h 55m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 3/1

9:45 pm-12:35 pm

1 stop11h 50m

George Town Owen Roberts Intl

Tue 3/3

2:00 pm-10:39 pm

1 stop11h 39m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 1/1

10:21 pm-2:21 pm

1 stop13h 00m

George Town Owen Roberts Intl

Tue 1/13

2:15 pm-11:29 pm

1 stop12h 14m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 1/9

9:45 pm-11:00 am

1 stop10h 15m

George Town Owen Roberts Intl

Sat 1/17

3:07 pm-10:39 pm

1 stop10h 32m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 11/9

10:10 pm-12:35 pm

1 stop11h 25m

George Town Owen Roberts Intl

Wed 11/12

1:50 pm-10:21 pm

1 stop11h 31m

$666

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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 month to book a flight from Portland to Cayman Islands?

Currently, January is the cheapest month in which you can book a flight from Portland to Cayman Islands (average of $467). Flying from Portland 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 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 September 17, 2025.

When flying from Portland to Cayman Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 17, 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
8,926 reviews

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
United Airlines
7.4
Good
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,926 reviews

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.

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, Air Canada, and Delta fly from Portland to Cayman Islands in about 11h 25m. The time it takes to get you to your destination can typically vary by up to 28h. 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.

  • What is the cheapest month to book a flight from Portland to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Portland to Cayman Islands (average of $467). Flying from Portland 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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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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Medford to Havana 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$578Average$838FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$608Average$799FlexibilityNo cancel feeOn-time71%

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