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Cheap flights from Portland to the Cayman Islands from $288

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland to the Cayman Islands departing on 1/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Portland to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
3:15 pm - 12:25 pm
PDX
-
GCM
18h 10m
2 stops
Air Canada Logo
1:30 pm - 9:15 am
GCM
-
PDX
22h 45m
2 stops
$565Air Canada
Sun, Mar 1 - Thu, Mar 5
Air Canada Logo
7:05 pm - 12:25 pm
PDX
-
GCM
38h 20m
2 stops
Air Canada Logo
1:30 pm - 6:30 pm
GCM
-
PDX
32h 00m
2 stops
$585Air Canada
Sun, Mar 1 - Thu, Mar 5
Air Canada Logo
7:05 pm - 12:25 pm
PDX
-
GCM
38h 20m
2 stops
Air Canada Logo
1:30 pm - 9:15 am
GCM
-
PDX
22h 45m
2 stops
$594Air Canada
Sun, Mar 1 - Thu, Mar 5
United Airlines Logo
11:28 pm - 12:45 pm
PDX
-
GCM
10h 17m
1 stop
United Airlines Logo
1:50 pm - 10:45 pm
GCM
-
PDX
10h 55m
1 stop
$687United Airlines
Sat, Mar 7 - Sat, Mar 14
Air Canada Logo
9:50 am - 11:10 am
PDX
-
GCM
23h 20m
2 stops
Air Canada Logo
12:30 pm - 9:15 am
GCM
-
PDX
22h 45m
2 stops
$689Air Canada
Wed, Apr 8 - Sun, Apr 12
United Airlines Logo
1:00 pm - 12:45 pm
PDX
-
GCM
20h 45m
2 stops
United Airlines Logo
4:30 pm - 11:51 am
GCM
-
PDX
21h 21m
2 stops
$692United Airlines
Sat, Mar 7 - Sat, Mar 14
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
26h 35m
1 stop
Multiple Airlines Logo
12:30 pm - 9:15 am
GCM
-
PDX
22h 45m
2 stops
$698Multiple Airlines
Wed, Apr 8 - Sun, Apr 12
American Airlines Logo
10:45 pm - 11:00 am
PDX
-
GCM
10h 15m
1 stop
American Airlines Logo
2:10 pm - 10:20 am
GCM
-
PDX
22h 10m
2 stops
$782American Airlines
Wed, Apr 8 - Sun, Apr 12
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
26h 35m
1 stop
Multiple Airlines Logo
4:45 pm - 8:35 pm
GCM
-
PDX
29h 50m
1 stop
$787Multiple Airlines
Wed, Apr 8 - Sun, Apr 12
United Airlines Logo
10:38 pm - 1:15 pm
PDX
-
GCM
11h 37m
1 stop
United Airlines Logo
2:50 pm - 10:45 pm
GCM
-
PDX
10h 55m
1 stop
$797United Airlines
Sun, Mar 1 - Thu, Mar 5

Air Canada flights from Portland to Cayman Islands

Our best Air Canada deals on Portland to Cayman Islands flight tickets
Air Canada
Mar 1
PDX3:15 pmPortland
18h 10m
2 stops
GCM12:25 pmGeorge Town Owen Roberts Intl
Mar 5
GCM1:30 pmGeorge Town Owen Roberts Intl
22h 45m
2 stops
PDX9:15 amPortland
$565
Air Canada
Mar 1
PDX7:05 pmPortland
38h 20m
2 stops
GCM12:25 pmGeorge Town Owen Roberts Intl
Mar 5
GCM1:30 pmGeorge Town Owen Roberts Intl
32h 00m
2 stops
PDX6:30 pmPortland
$585
Air Canada
Mar 1
PDX7:05 pmPortland
38h 20m
2 stops
GCM12:25 pmGeorge Town Owen Roberts Intl
Mar 5
GCM1:30 pmGeorge Town Owen Roberts Intl
22h 45m
2 stops
PDX9:15 amPortland
$594

United Airlines flights from Portland to Cayman Islands

Our best United Airlines deals on Portland to Cayman Islands flight tickets
United Airlines
Mar 7
PDX11:28 pmPortland
10h 17m
1 stop
GCM12:45 pmGeorge Town Owen Roberts Intl
Mar 14
GCM1:50 pmGeorge Town Owen Roberts Intl
10h 55m
1 stop
PDX10:45 pmPortland
$687
United Airlines
Mar 7
PDX1:00 pmPortland
20h 45m
2 stops
GCM12:45 pmGeorge Town Owen Roberts Intl
Mar 14
GCM4:30 pmGeorge Town Owen Roberts Intl
21h 21m
2 stops
PDX11:51 amPortland
$692
United Airlines
Mar 1
PDX11:59 pmPortland
10h 46m
1 stop
GCM1:45 pmGeorge Town Owen Roberts Intl
Mar 5
GCM2:50 pmGeorge Town Owen Roberts Intl
10h 55m
1 stop
PDX10:45 pmPortland
$797

momondo 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, momondo users made 832,500 searches. Data last updated January 21, 2026.
Use the filters below to find and compare flights from Portland to the Cayman Islands that are best for you.

Fly from

Fly to

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

Sun 3/1

7:05 pm-12:25 pm

2 stops38h 20m

George Town Owen Roberts Intl

Thu 3/5

1:30 pm-6:30 pm

2 stops32h 00m

$585

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 3/1

7:05 pm-12:25 pm

2 stops38h 20m

George Town Owen Roberts Intl

Thu 3/5

1:30 pm-9:15 am

2 stops22h 45m

$594

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

Sat 3/7

1:00 pm-12:45 pm

2 stops20h 45m

George Town Owen Roberts Intl

Sat 3/14

4:30 pm-11:51 am

2 stops21h 21m

$692

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

Wed 4/8

7:00 am-11:35 am

1 stop26h 35m

George Town Owen Roberts Intl

Sun 4/12

4:45 pm-8:35 pm

1 stop29h 50m

$787

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

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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See travel insights to the Cayman Islands from

How to get the cheapest flight ticket from Portland to Cayman Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Cayman Islands?

If you aren’t able to travel to Cayman Islands during the month of January, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $745.

Cheap Portland to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland to Cayman Islands

Fastest flight time

10h 26m

Direct flights

None
The fastest flight from Portland to Cayman Islands takes 10h 26m
There are no direct flights from Portland to Cayman Islands. There are no popular flight routes from Portland to Cayman Islands.
Search flight deals

  • When did momondo last update prices for flights from Portland Airport to Cayman Islands?

    Prices for flights from Portland Airport to Cayman Islands were last updated today.

  • How many operators does momondo search for flights from Portland Airport to Cayman Islands?

  • How old do you have to be to fly from Portland Airport to Cayman Islands?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Portland Airport to Cayman Islands.

  • What documentation or ID do you need to fly to Cayman Islands?

    The required travel and health documents for your Cayman Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Cayman Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Portland to Cayman Islands

Compare and see reviews for airlines that fly from Portland to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $666Free CancellationRating
7.2
11,169 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Cayman Islands?

It is quick and easy to find Portland to Cayman Islands flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Cayman Islands that suits you.

Can I find flights from Portland to Cayman Islands with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Cayman Islands from Portland with this policy.

How can momondo help me find flights from Portland to Cayman Islands?

Once all potential Portland to Cayman Islands flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Portland to Cayman Islands right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Portland to Cayman Islands flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the Cayman Islands

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