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Grand Cayman

$281+ 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
nov. 13 — nov. 201
jue. 11/13
jue. 11/20
1 adult, Economy
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Find 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 octubre 14, 2025.

This Expedia deal was found by Cheapflights users on 10/14. 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.
vie. 11/287:00 pmPDX - GCM
2 stops38h 25mAir Canada
vie. 12/51:30 pmGCM - PDX
2 stops28h 10mAir Canada
Deal found 10/14$618
This American Airlines deal was found by Cheapflights users on 10/14. 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.
vie. 11/1410:15 pmPDX - GCM
1 stop13h 13mAmerican Airlines
mar. 11/1812:55 pmGCM - PDX
1 stop10h 23mAmerican Airlines
Deal found 10/14$666
This American Airlines deal was found by Cheapflights users on 10/14. 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.
vie. 11/2810:15 pmPDX - GCM
2 stops13h 31mAmerican Airlines
vie. 12/58:45 amGCM - PDX
1 stop18h 07mAmerican Airlines
Deal found 10/14$670
This Delta deal was found by Cheapflights users on 10/13. 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.
vie. 11/145:17 pmPDX - GCM
2 stops16h 08mDelta
mar. 11/181:50 pmGCM - PDX
1 stop11h 31mDelta
Deal found 10/13$671
This American Airlines deal was found by Cheapflights users on 10/14. 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.
jue. 11/2010:45 pmPDX - GCM
1 stop18h 43mAmerican Airlines
jue. 11/271:25 pmGCM - PDX
1 stop13h 06mAmerican Airlines
Deal found 10/14$705
This Air Canada deal was found by Cheapflights users on 10/14. 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.
jue. 11/203:15 pmPDX - GCM
2 stops18h 10mAir Canada
jue. 11/271:30 pmGCM - PDX
2 stops22h 45mAir Canada
Deal found 10/14$722
This United Airlines deal was found by Cheapflights users on 10/13. 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.
vie. 11/147:38 pmPDX - GCM
2 stops15h 07mUnited Airlines
mar. 11/185:45 pmGCM - PDX
3 stops20h 08mUnited Airlines
Deal found 10/13$781
This Mytrip deal was found by Cheapflights users on 10/14. 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.
jue. 11/203:15 pmPDX - GCM
3 stops18h 10mMultiple Airlines
jue. 11/271:30 pmGCM - PDX
3 stops22h 45mMultiple Airlines
Deal found 10/14$857
This United Airlines deal was found by Cheapflights users on 10/13. 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.
sáb. 12/2711:55 pmPDX - GCM
1 stop10h 50mUnited Airlines
sáb. 1/35:45 pmGCM - PDX
2 stops26h 46mUnited Airlines
Deal found 10/13$1,262
This American Airlines deal was found by Cheapflights users on 10/13. 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.
jue. 11/2010:45 pmPDX - GCM
1 stop18h 43mAmerican Airlines
sáb. 11/299:00 amGCM - PDX
1 stop17h 31mAmerican Airlines
Deal found 10/13$1,272

Cheap 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 octubre 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$618
(Expedia)

One-way from

$281
(American Airlines)

Popular in

February

Cheapest in

January

Average price

$761
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
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One-way flight from Portland to Grand Cayman
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Highest demand for flights based on searches. 1% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 octubre 14, 2025.
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

dom. 3/1

9:45 pm-12:35 pm

1 stop11h 50m

George Town Owen Roberts Intl

mar. 3/3

2:00 pm-10:39 pm

1 stop11h 39m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

vie. 11/14

10:15 pm-11:57 am

1 stop10h 42m

George Town Owen Roberts Intl

mar. 11/18

12:55 pm-8:18 pm

1 stop10h 23m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

vie. 11/28

10:15 pm-2:46 pm

2 stops13h 31m

George Town Owen Roberts Intl

vie. 12/5

8:45 am-11:52 pm

1 stop18h 07m

$670

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

mié. 12/17

11:59 pm-4:00 pm

2 stops13h 01m

George Town Owen Roberts Intl

mié. 12/24

5:45 pm-10:01 am

2 stops19h 16m

$671

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

vie. 11/14

5:17 pm-12:25 pm

2 stops16h 08m

George Town Owen Roberts Intl

mar. 11/18

1:50 pm-10:21 pm

1 stop11h 31m

$671

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

mié. 12/17

10:45 pm-11:50 am

1 stop10h 05m

George Town Owen Roberts Intl

mié. 12/24

7:30 am-9:19 pm

2 stops16h 49m

$671

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

jue. 11/20

10:45 pm-8:28 pm

1 stop18h 43m

George Town Owen Roberts Intl

jue. 11/27

1:25 pm-11:31 pm

1 stop13h 06m

$705

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

mié. 1/28

6:00 am-8:23 pm

2 stops11h 23m

$281

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

mié. 1/28

7:45 am-1:45 pm

3 stops27h 00m

$336

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

mar. 1/27

12:55 am-1:44 pm

2 stops33h 49m

$1,790

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

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, December is the cheapest month in which you can book a flight from Portland to Grand Cayman (average of $455). Flying from Portland to Grand Cayman in August is currently the most expensive (average of $801). 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 LAW?

Find hourly flight availability from Portland to Grand Cayman. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 14, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 33% on flights from Portland to Grand Cayman by exploring options for tickets in the afternoon.

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 octubre 14, 2025.
Get a feel of what it's like to fly with United Airlines and 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.
United Airlines
7.4
Good
8,976 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,976 reviews
United Airlines
7.4
Good
8,976 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
American Airlines
7.2
Good
11,042 reviews
United Airlines
7.4
Good
8,976 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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 $666, Delta can have you in Grand Cayman from Portland in 10h 42m. 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, December is the cheapest month in which you can book a flight from Portland to Grand Cayman (average of $455). Flying from Portland to Grand Cayman in August is currently the most expensive (average of $801). 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
Eugene to George Town flights
Medford to George Town flights

Top 2 airlines flying from Portland to Grand Cayman

Discover the top 2 airlines 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 octubre 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$578Average$838FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$608Average$802FlexibilityNo cancel feeOn-time71%

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