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Grand Cayman

$288+ Cheap flights from Portland (PDX) to Grand Cayman

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Portland to Grand Cayman

Cheapest flights from Portland to Grand Cayman
Explore the most affordable flight options available from Portland to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Air Canada deal was found by Cheapflights users on 1/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/13:15 pm
PDX
-
GCM
2 stops18h 10m
Air Canada
Thu 3/51:30 pm
GCM
-
PDX
2 stops22h 45m
Air Canada
Deal found 1/20$565
This Delta deal was found by Cheapflights users on 1/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:30 pm
PDX
-
GCM
1 stop19h 10m
Delta
Thu 10/2912:55 pm
GCM
-
PDX
1 stop11h 31m
Delta
Deal found 1/18$687
This Air Canada deal was found by Cheapflights users on 1/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/89:50 am
PDX
-
GCM
2 stops23h 20m
Air Canada
Sun 4/1212:30 pm
GCM
-
PDX
2 stops22h 45m
Air Canada
Deal found 1/19$689
This Delta deal was found by Cheapflights users on 1/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:38 pm
PDX
-
GCM
2 stops20h 02m
Delta
Thu 10/2912:55 pm
GCM
-
PDX
2 stops12h 56m
Delta
Deal found 1/18$692
This American Airlines deal was found by Cheapflights users on 1/19. 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.
Sun 11/15:42 pm
PDX
-
GCM
2 stops15h 16m
American Airlines
Sun 11/83:14 pm
GCM
-
PDX
1 stop11h 37m
American Airlines
Deal found 1/19$697
This Expedia deal was found by Cheapflights users on 1/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:00 am
PDX
-
GCM
1 stop26h 35m
Multiple Airlines
Sun 4/1212:30 pm
GCM
-
PDX
2 stops22h 45m
Multiple Airlines
Deal found 1/19$698
This American Airlines deal was found by Cheapflights users on 1/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/810:45 pm
PDX
-
GCM
1 stop10h 15m
American Airlines
Sun 4/122:10 pm
GCM
-
PDX
2 stops22h 10m
American Airlines
Deal found 1/20$782

Find flight deals from Portland to Grand Cayman

Keep the following information in mind while searching for Portland to Grand Cayman flight deals. Data was last updated January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$565
(Air Canada)

One-way from

$288
(Air Canada)

Popular in

March

Cheapest in

January

Average price

$666
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 Grand Cayman
Search Deals
One-way flight from Portland to Grand Cayman
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($90 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Grand Cayman 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 January 21, 2026.
Use the filters below to find and compare flights from Portland to Grand Cayman that are best for you.

Fly from

Portland

Fly to

Grand Cayman

Route

Depart

Return

Price

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 3/1

3:15 pm-12:25 pm

2 stops18h 10m

George Town Owen Roberts Intl

Thu 3/5

1:30 pm-9:15 am

2 stops22h 45m

$565

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sat 3/7

11:28 pm-12:45 pm

1 stop10h 17m

George Town Owen Roberts Intl

Sat 3/14

1:50 pm-10:45 pm

1 stop10h 55m

$687

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 4/8

9:50 am-11:10 am

2 stops23h 20m

George Town Owen Roberts Intl

Sun 4/12

12:30 pm-9:15 am

2 stops22h 45m

$689

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 4/8

7:00 am-11:35 am

1 stop26h 35m

George Town Owen Roberts Intl

Sun 4/12

12:30 pm-9:15 am

2 stops22h 45m

$698

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 4/8

10:45 pm-11:00 am

1 stop10h 15m

George Town Owen Roberts Intl

Sun 4/12

2:10 pm-10:20 am

2 stops22h 10m

$782

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 3/1

10:38 pm-1:15 pm

1 stop11h 37m

George Town Owen Roberts Intl

Thu 3/5

2:50 pm-10:45 pm

1 stop10h 55m

$797

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 1/28

7:00 pm-12:25 pm

2 stops14h 25m

$288

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 1/28

9:45 pm-12:40 pm

1 stop11h 55m

$376

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 1/28

11:07 pm-2:45 pm

1 stop12h 38m

$376

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 1/28

7:45 am-1:45 pm

3 stops27h 00m

$431

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 12 results
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Best time to book a flight from Portland to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman 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 Grand Cayman

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

Currently, July is the cheapest month in which you can book a flight from Portland to Grand Cayman (average of $609). Flying from Portland to Grand Cayman in March is currently the most expensive (average of $809). 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.

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated January 21, 2026.
Get a feel of what it's like to fly with American Airlines from Portland to Grand Cayman by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,169 reviews

Boarding

7.5

Entertainment

6.9

Crew

8.0

Overall

7.2

Comfort

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,169 reviews
American Airlines
7.2
Good
11,169 reviews

Boarding

7.5

Entertainment

6.9

Crew

8.0

Overall

7.2

Comfort

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Portland to Grand Cayman. 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 Grand Cayman?

    Most people fly from Portland (PDX) if they book a flight from Portland to Grand Cayman. Portland is conveniently located just 6.0 mi from Portland’s city center.

  • How long is the flight from Portland to Grand Cayman?

    For as low as $687, Air Canada can have you in Grand Cayman from Portland in 10h 17m. Airlines will cover a distance of 2961 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Portland to Grand Cayman that include hotel bookings?

    Yes. In addition to deals on Portland to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Grand Cayman?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Grand Cayman.

  • Can I find deals for business class flights from Portland to Grand Cayman?

    Yes. Cheapflights offers flight deals from Portland to Grand Cayman 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 Grand Cayman?

    Currently, July is the cheapest month in which you can book a flight from Portland to Grand Cayman (average of $609). Flying from Portland to Grand Cayman in March is currently the most expensive (average of $809). 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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Alternative routes for Portland to Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
Portland to George Town flights
Boise to George Town flights
Medford to George Town flights
Eugene to George Town flights

Top airline flying from Portland to Grand Cayman

Discover the top airline that operate flights from Portland to Grand Cayman. 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$666Average$819FlexibilityNo cancel feeOn-time71%

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