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Cayman Islands

$603+ 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 7/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$603
(Mytrip)

Popular in

February

Cheapest in

January

Average price

$746
From Portland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/12. 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 7/36:39 pmPDX - GCM
2 stops15h 01mMultiple Airlines
Tue 7/811:30 amGCM - PDX
2 stops23h 48mMultiple Airlines
Deal found 6/12$603
This Delta deal was found by Cheapflights users on 6/10. 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.
Fri 8/2910:05 pmPDX - GCM
1 stop11h 32mDelta
Sat 9/612:52 pmGCM - PDX
1 stop11h 20mDelta
Deal found 6/10$666
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/167:05 pmPDX - GCM
2 stops38h 15mAir Canada
Sun 11/231:35 pmGCM - PDX
2 stops22h 59mAir Canada
Deal found 6/12$716
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 8/1511:59 pmPDX - GCM
1 stop11h 16mAmerican Airlines
Fri 8/2212:25 pmGCM - PDX
1 stop9h 51mAmerican Airlines
Deal found 6/11$785
This United Airlines deal was found by Cheapflights users on 6/12. 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 7/36:43 pmPDX - GCM
2 stops40h 47mUnited Airlines
Tue 7/81:35 pmGCM - PDX
1 stop10h 58mUnited Airlines
Deal found 6/12$793
This Southwest deal was found by Cheapflights users on 6/11. 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 12/218:00 pmPDX - GCM
2 stops13h 35mSouthwest
Sun 1/41:30 pmGCM - PDX
2 stops13h 55mSouthwest
Deal found 6/11$1,080

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 June 12, 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

Thu 7/3

6:39 pm-11:40 am

2 stops15h 01m

George Town Owen Roberts Intl

Tue 7/8

11:30 am-9:18 am

2 stops23h 48m

$603

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 8/29

10:05 pm-11:37 am

1 stop11h 32m

George Town Owen Roberts Intl

Sat 9/6

12:52 pm-10:12 pm

1 stop11h 20m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 11/16

7:05 pm-12:20 pm

2 stops38h 15m

George Town Owen Roberts Intl

Sun 11/23

1:35 pm-9:34 am

2 stops22h 59m

$716

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 8/15

11:59 pm-1:15 pm

1 stop11h 16m

George Town Owen Roberts Intl

Fri 8/22

12:25 pm-8:16 pm

1 stop9h 51m

$785

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 7/3

6:43 pm-1:30 pm

2 stops40h 47m

George Town Owen Roberts Intl

Tue 7/8

1:35 pm-10:33 pm

1 stop10h 58m

$793

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 June 12, 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 June 12, 2025.
Delta
8.0
Very good
7,946 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

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
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

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
8,790 reviews
Delta
8.0
Very good
7,946 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

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
7,946 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

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!
Air Canada
7.1
Good
9,537 reviews
Delta
8.0
Very good
7,946 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

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 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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Redmond to Havana flights
Portland to Georgetown flights
Redmond to Montego Bay flights
Medford to Havana flights
Eugene to Bridgetown flights
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Portland to Gregory Town flights
Boise to Georgetown flights
Boise to George Town flights
Boise to Holguín flights
Portland to Holguín flights
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Portland to Port of Spain flights
Boise to Port Royal flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$561Average$728FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$576Average$825FlexibilityNo cancel feeOn-time69%

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