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Cayman Islands

$625+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
Jul 12 — Jul 191
Sat 7/12
Sat 7/19
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 July 7, 2025.

Round-trip from

$625
(Orbitz)

Popular in

September

Cheapest in

January

Average price

$659
From Portland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 7, 2025.

This Orbitz deal was found by Cheapflights users on 7/7. 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.
Wed 11/199:50 amPDX - GCM
2 stops23h 30mMultiple Airlines
Tue 11/2511:30 amGCM - PDX
1 stop11h 53mMultiple Airlines
Deal found 7/7$625
This Southwest deal was found by Cheapflights users on 7/7. 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 11/192:35 pmPDX - GCM
2 stops19h 00mSouthwest
Tue 11/251:30 pmGCM - PDX
2 stops14h 35mSouthwest
Deal found 7/7$640
This Delta deal was found by Cheapflights users on 7/7. 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 11/199:45 pmPDX - GCM
1 stop11h 52mDelta
Tue 11/252:02 pmGCM - PDX
1 stop11h 30mDelta
Deal found 7/7$666
This United Airlines deal was found by Cheapflights users on 7/7. 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 8/611:59 pmPDX - GCM
1 stop10h 31mUnited Airlines
Wed 8/131:35 pmGCM - PDX
1 stop10h 58mUnited Airlines
Deal found 7/7$766
This American Airlines deal was found by Cheapflights users on 7/7. 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 12/2311:00 pmPDX - GCM
1 stop17h 51mAmerican Airlines
Wed 12/312:15 pmGCM - PDX
1 stop11h 54mAmerican Airlines
Deal found 7/7$785

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 July 7, 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

Wed 11/19

9:50 am-12:20 pm

2 stops23h 30m

George Town Owen Roberts Intl

Tue 11/25

11:30 am-8:23 pm

1 stop11h 53m

$625

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 11/19

2:35 pm-12:35 pm

2 stops19h 00m

George Town Owen Roberts Intl

Tue 11/25

1:30 pm-1:05 am

2 stops14h 35m

$640

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 11/19

9:45 pm-12:37 pm

1 stop11h 52m

George Town Owen Roberts Intl

Tue 11/25

2:02 pm-10:32 pm

1 stop11h 30m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 8/6

11:59 pm-12:30 pm

1 stop10h 31m

George Town Owen Roberts Intl

Wed 8/13

1:35 pm-10:33 pm

1 stop10h 58m

$766

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 12/23

11:00 pm-7:51 pm

1 stop17h 51m

George Town Owen Roberts Intl

Wed 12/31

2:15 pm-11:09 pm

1 stop11h 54m

$785

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

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 July 7, 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 July 7, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,257 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,962 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,844 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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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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 July 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$561Average$742FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$576Average$838FlexibilityNo cancel feeOn-time69%

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