HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Cayman Islands

$235+ Cheap flights from Portland (PDX) to the Cayman Islands

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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Cayman Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$551
(Air Canada)

One-way from

$235
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$666
Provider with most accurate pricing for Portland-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-George Town Owen Roberts Intl flights.
Search Deals
From Portland to Cayman Islands
Search Deals
One-way flight from Portland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($128 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 8, 2026.

This Air Canada deal was found by Cheapflights users on 1/6. 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 4/227:05 pmPDX - GCM
2 stops38h 05mAir Canada
Sat 5/212:25 pmGCM - PDX
2 stops23h 05mAir Canada
Deal found 1/6$551
This Orbitz deal was found by Cheapflights users on 1/6. 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.
Sun 2/19:50 amPDX - GCM
2 stops23h 35mAir Canada
Thu 2/51:30 pmGCM - PDX
2 stops28h 10mAir Canada
Deal found 1/6$554
This Expedia deal was found by Cheapflights users on 1/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/167:00 amPDX - GCM
1 stop12h 15mMultiple Airlines
Mon 3/234:45 pmGCM - PDX
1 stop29h 50mMultiple Airlines
Deal found 1/7$562
This Air Canada deal was found by Cheapflights users on 1/6. 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 1/189:50 amPDX - GCM
2 stops23h 35mAir Canada
Thu 1/221:30 pmGCM - PDX
2 stops32h 00mAir Canada
Deal found 1/6$576
This Expedia deal was found by Cheapflights users on 1/6. 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.
Sun 2/17:00 amPDX - GCM
1 stop25h 35mMultiple Airlines
Thu 2/51:30 pmGCM - PDX
2 stops28h 10mMultiple Airlines
Deal found 1/6$604
This Air Canada deal was found by Cheapflights users on 1/8. 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 1/113:15 pmPDX - GCM
2 stops42h 10mAir Canada
Thu 1/151:30 pmGCM - PDX
2 stops32h 00mAir Canada
Deal found 1/8$648
This Expedia deal was found by Cheapflights users on 1/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/173:15 pmPDX - GCM
2 stops42h 10mAir Canada
Mon 3/3012:30 pmGCM - PDX
2 stops32h 00mAir Canada
Deal found 1/7$664
This Expedia deal was found by Cheapflights users on 1/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/177:00 amPDX - GCM
1 stop31h 05mMultiple Airlines
Mon 3/3012:30 pmGCM - PDX
2 stops32h 00mMultiple Airlines
Deal found 1/7$665

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 January 8, 2026.
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 4/22

7:05 pm-11:10 am

2 stops38h 05m

George Town Owen Roberts Intl

Sat 5/2

12:25 pm-9:30 am

2 stops23h 05m

$551

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 2/1

9:50 am-12:25 pm

2 stops23h 35m

George Town Owen Roberts Intl

Thu 2/5

1:30 pm-2:40 pm

2 stops28h 10m

$554

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 3/16

7:00 am-9:15 pm

1 stop12h 15m

George Town Owen Roberts Intl

Mon 3/23

4:45 pm-11:44 pm

2 stops32h 59m

$564

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 1/18

9:50 am-12:25 pm

2 stops23h 35m

George Town Owen Roberts Intl

Thu 1/22

1:30 pm-6:30 pm

2 stops32h 00m

$576

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 2/1

7:00 am-11:35 am

1 stop25h 35m

George Town Owen Roberts Intl

Thu 2/5

1:30 pm-2:40 pm

2 stops28h 10m

$604

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 3/17

7:00 am-4:05 pm

1 stop31h 05m

George Town Owen Roberts Intl

Mon 3/30

12:30 pm-6:30 pm

2 stops32h 00m

$665

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 2/20

11:35 pm-3:00 pm

1 stop12h 25m

George Town Owen Roberts Intl

Fri 2/27

3:45 pm-11:50 pm

1 stop11h 05m

$667

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 2/20

6:57 pm-4:20 pm

2 stops18h 23m

George Town Owen Roberts Intl

Fri 2/27

2:50 pm-10:40 pm

1 stop10h 50m

$667

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 3/19

11:59 pm-2:25 pm

1 stop12h 26m

George Town Owen Roberts Intl

Thu 3/26

12:00 pm-8:44 pm

1 stop10h 44m

$667

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sat 1/31

5:51 pm-2:00 pm

2 stops17h 09m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 15 results
1
2

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, July is the cheapest month in which you can book a flight from Portland to Cayman Islands (average of $609). Flying from Portland to Cayman Islands 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 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 January 8, 2026.
Read reviews from past customers who have flown 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.
American Airlines
7.2
Good
11,094 reviews

Boarding

7.5

Comfort

7.2

Food

6.4

Crew

8.0

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,094 reviews
American Airlines
7.2
Good
11,094 reviews

Boarding

7.5

Comfort

7.2

Food

6.4

Crew

8.0

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 Air Canada fly from Portland to Cayman Islands in about 38h 05m. The time it takes to get you to your destination can typically vary by up to . The distance between Portland and Cayman Islands is about 2961 mi.

  • 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, July is the cheapest month in which you can book a flight from Portland to Cayman Islands (average of $609). Flying from Portland to Cayman Islands 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
Portland to Luis Munoz Marin Intl flights
Portland to Saint Thomas Island flights
Boise to Luis Munoz Marin Intl flights
Portland to Nassau flights
Portland to Punta Cana flights
Portland to Road Town flights
Portland to Santo Domingo flights
Portland to Oranjestad flights
Portland to Simpson Bay flights
Medford to Luis Munoz Marin Intl flights
Portland to Providenciales flights
Boise to Saint Thomas Island flights
Portland to Santiago de los Caballeros flights
Portland to Montego Bay flights
Boise to Nassau flights
Portland to Christiansted flights
Portland to George Town flights
Boise to Punta Cana flights
Portland to Kralendijk flights
Portland to Castries flights
Eugene to Luis Munoz Marin Intl flights
Portland to Willemstad flights
Portland to St. John's flights
Portland to Basseterre flights
Boise to Santo Domingo flights
Portland to Georgetown flights
Boise to Montego Bay flights
Portland to Bridgetown flights
Portland to Kingston flights
Boise to Bridgetown flights
Eugene to Punta Cana flights
Boise to Oranjestad flights
Boise to George Town flights
Redmond to Nassau flights
Portland to Fort-de-France flights
Portland to Havana flights
Redmond to Montego Bay flights
Redmond to Santo Domingo flights
Portland to Puerto Plata flights
Boise to Castries flights
Portland to St. George's flights
Medford to George Town flights
Boise to Havana flights
Eugene to George Town flights
Portland to Port of Spain flights
Redmond to Havana flights
Portland to Rock Sound flights
Portland to Freeport flights
Boise to Georgetown flights

Top airline flying from Portland to Cayman Islands

Discover the top airline 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$640Average$806FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.