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Cayman Islands

$615+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$615
(Mytrip)

Popular in

November

Cheapest in

January

Average price

$626
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 Portland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($162 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($44 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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.
Wed 4/26:13 pmPDX - GCM
2 stops25h 07mMultiple Airlines
Sun 4/65:00 pmGCM - PDX
2 stops26h 55mMultiple Airlines
Deal found 2/19$615
This Delta deal was found by Cheapflights users on 2/19. 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 5/311:19 pmPDX - GCM
1 stop10h 03mDelta
Wed 5/1412:51 pmGCM - PDX
1 stop11h 36mDelta
Deal found 2/19$663
This United Airlines deal was found by Cheapflights users on 2/19. 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 4/57:35 pmPDX - GCM
2 stops15h 05mUnited Airlines
Sat 4/124:15 pmGCM - PDX
2 stops19h 32mUnited Airlines
Deal found 2/19$717
This Southwest deal was found by Cheapflights users on 2/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/215:25 pmPDX - GCM
2 stops16h 25mSouthwest
Wed 5/2812:45 pmGCM - PDX
2 stops12h 40mSouthwest
Deal found 2/18$745
This American Airlines deal was found by Cheapflights users on 2/19. 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 6/231:44 amPDX - GCM
1 stop9h 35mAmerican Airlines
Thu 7/33:45 pmGCM - PDX
1 stop8h 53mAmerican Airlines
Deal found 2/19$750
This Justfly.com deal was found by Cheapflights users on 2/18. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/216:15 amPDX - GCM
2 stops27h 40mAir Canada
Mon 5/2612:50 pmGCM - PDX
2 stops27h 50mAir Canada
Deal found 2/18$764
This WestJet deal was found by Cheapflights users on 2/20. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3112:40 amPDX - GCM
2 stops34h 05mWestJet
Sat 8/91:45 pmGCM - PDX
2 stops25h 07mWestJet
Deal found 2/20$2,126

Find flights from Portland to Cayman Islands within your budget

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 February 20, 2025.

Fly from

Portland

Fly to

Cayman Islands

Route

Depart

Return

Price

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 4/2

6:13 pm-9:20 pm

2 stops25h 07m

George Town Owen Roberts Intl

Sun 4/6

5:00 pm-5:55 pm

2 stops26h 55m

$615

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sat 5/3

11:19 pm-11:22 am

1 stop10h 03m

George Town Owen Roberts Intl

Wed 5/14

12:51 pm-10:27 pm

1 stop11h 36m

$663

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sat 4/5

7:35 pm-12:40 pm

2 stops15h 05m

George Town Owen Roberts Intl

Sat 4/12

4:15 pm-9:47 am

2 stops19h 32m

$717

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 5/21

5:25 pm-11:50 am

2 stops16h 25m

George Town Owen Roberts Intl

Wed 5/28

12:45 pm-11:25 pm

2 stops12h 40m

$745

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 6/23

1:44 am-1:19 pm

1 stop9h 35m

George Town Owen Roberts Intl

Thu 7/3

3:45 pm-10:38 pm

1 stop8h 53m

$750

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 5/21

6:15 am-11:55 am

2 stops27h 40m

George Town Owen Roberts Intl

Mon 5/26

12:50 pm-2:40 pm

2 stops27h 50m

$764

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 7/31

12:40 am-12:45 pm

2 stops34h 05m

George Town Owen Roberts Intl

Sat 8/9

1:45 pm-12:52 pm

2 stops25h 07m

$2,126

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Portland to Cayman Islands

Get recent, data-driven insights about flights from Portland to Cayman Islands including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

WestJet
7.2
Good
2,801 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

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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 3 airlines flying from Portland to Cayman Islands

Discover the top 3 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$506Average$624FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$553Average$688FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$576Average$775FlexibilityNo cancel feeOn-time69%
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