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Cheap flights from Portland to the Cayman Islands from $525

This is the cheapest round-trip 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 10/18. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
10:10 am - 11:30 am
PDX
-
GCM
23h 20m
2 stops
Air Canada Logo
12:10 pm - 9:26 am
GCM
-
PDX
23h 16m
2 stops
$525Air Canada
Sun, Oct 18 - Sun, Oct 25
Multiple Airlines Logo
7:45 pm - 11:30 am
PDX
-
GCM
37h 45m
2 stops
Multiple Airlines Logo
6:10 pm - 12:59 pm
GCM
-
PDX
20h 49m
1 stop
$658Multiple Airlines
Thu, Sep 17 - Sun, Sep 27
Southwest Logo
1:00 pm - 12:35 pm
PDX
-
GCM
20h 35m
2 stops
Southwest Logo
1:30 pm - 11:15 pm
GCM
-
PDX
12h 45m
2 stops
$682Southwest
Tue, Nov 3 - Wed, Nov 11
Southwest Logo
9:20 pm - 11:55 am
PDX
-
GCM
12h 35m
2 stops
Southwest Logo
12:50 pm - 12:15 am
GCM
-
PDX
13h 25m
2 stops
$687Southwest
Tue, Jul 7 - Sun, Jul 12
Southwest Logo
11:30 pm - 11:55 am
PDX
-
GCM
10h 25m
2 stops
Southwest Logo
12:50 pm - 11:55 pm
GCM
-
PDX
13h 05m
2 stops
$692Southwest
Thu, Jul 30 - Mon, Aug 3
Air Canada Logo
3:30 pm - 11:30 am
PDX
-
GCM
18h 00m
2 stops
Air Canada Logo
12:25 pm - 9:31 am
GCM
-
PDX
23h 06m
2 stops
$698Air Canada
Fri, Sep 18 - Thu, Sep 24
Air Canada Logo
3:30 pm - 11:30 am
PDX
-
GCM
42h 00m
2 stops
Air Canada Logo
12:25 pm - 2:51 pm
GCM
-
PDX
28h 26m
2 stops
$712Air Canada
Tue, Sep 15 - Thu, Sep 24
Multiple Airlines Logo
6:19 am - 4:05 pm
PDX
-
GCM
31h 46m
2 stops
Multiple Airlines Logo
4:00 pm - 11:41 am
GCM
-
PDX
21h 41m
1 stop
$724Multiple Airlines
Mon, Aug 17 - Sat, Aug 22
Multiple Airlines Logo
9:30 pm - 2:45 pm
PDX
-
GCM
15h 15m
1 stop
Multiple Airlines Logo
12:10 pm - 6:31 pm
GCM
-
PDX
32h 21m
2 stops
$731Multiple Airlines
Sun, Oct 18 - Sun, Oct 25
Air Canada Logo
10:00 am - 12:00 pm
PDX
-
GCM
23h 00m
2 stops
Air Canada Logo
1:10 pm - 9:26 am
GCM
-
PDX
23h 16m
2 stops
$750Air Canada
Tue, Nov 3 - Wed, Nov 11

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Air Canada flights from Portland to Cayman Islands

Our best Air Canada deals on Portland to Cayman Islands flight tickets
Air Canada
Oct 18
PDX10:10 amPortland
23h 20m
2 stops
GCM11:30 amGeorge Town Owen Roberts Intl
Oct 25
GCM12:10 pmGeorge Town Owen Roberts Intl
23h 16m
2 stops
PDX9:26 amPortland
$525
Air Canada
Sep 18
PDX3:30 pmPortland
18h 00m
2 stops
GCM11:30 amGeorge Town Owen Roberts Intl
Sep 24
GCM12:25 pmGeorge Town Owen Roberts Intl
23h 06m
2 stops
PDX9:31 amPortland
$698
Air Canada
Sep 15
PDX3:30 pmPortland
42h 00m
2 stops
GCM11:30 amGeorge Town Owen Roberts Intl
Sep 24
GCM12:25 pmGeorge Town Owen Roberts Intl
28h 26m
2 stops
PDX2:51 pmPortland
$712

American Airlines flights from Portland to Cayman Islands

Our best American Airlines deals on Portland to Cayman Islands flight tickets
American Airlines
Jul 30
PDX11:41 pmPortland
11h 55m
1 stop
GCM1:36 pmGeorge Town Owen Roberts Intl
Aug 3
GCM12:33 pmGeorge Town Owen Roberts Intl
10h 07m
1 stop
PDX8:40 pmPortland
$781
American Airlines
Aug 14
PDX10:59 pmPortland
10h 31m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
Aug 27
GCM12:30 pmGeorge Town Owen Roberts Intl
12h 39m
2 stops
PDX11:09 pmPortland
$786
American Airlines
Jul 1
PDX5:33 pmPortland
15h 28m
2 stops
GCM11:01 amGeorge Town Owen Roberts Intl
Jul 7
GCM5:10 pmGeorge Town Owen Roberts Intl
21h 39m
2 stops
PDX12:49 pmPortland
$799

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 June 8, 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

Cheapest round-trip

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 10/18

10:10 am-11:30 am

2 stops23h 20m

George Town Owen Roberts Intl

Sun 10/25

12:10 pm-9:26 am

2 stops23h 16m

$525

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 9/17

7:45 pm-11:30 am

2 stops37h 45m

George Town Owen Roberts Intl

Sun 9/27

6:10 pm-12:59 pm

1 stop20h 49m

$658

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 11/3

1:00 pm-12:35 pm

2 stops20h 35m

George Town Owen Roberts Intl

Wed 11/11

1:30 pm-11:15 pm

2 stops12h 45m

$682

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 7/7

9:20 pm-11:55 am

2 stops12h 35m

George Town Owen Roberts Intl

Sun 7/12

12:50 pm-12:15 am

2 stops13h 25m

$687
Quickest round-trip

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 7/30

11:30 pm-11:55 am

2 stops10h 25m

George Town Owen Roberts Intl

Mon 8/3

12:50 pm-11:55 pm

2 stops13h 05m

$692

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 9/18

3:30 pm-11:30 am

2 stops18h 00m

George Town Owen Roberts Intl

Thu 9/24

12:25 pm-9:31 am

2 stops23h 06m

$698

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 9/15

3:30 pm-11:30 am

2 stops42h 00m

George Town Owen Roberts Intl

Thu 9/24

12:25 pm-2:51 pm

2 stops28h 26m

$712

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 8/17

6:19 am-4:05 pm

2 stops31h 46m

George Town Owen Roberts Intl

Sat 8/22

4:00 pm-11:41 am

1 stop21h 41m

$724

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 10/18

9:30 pm-2:45 pm

1 stop15h 15m

George Town Owen Roberts Intl

Sun 10/25

12:10 pm-6:31 pm

2 stops32h 21m

$731

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 11/3

10:00 am-12:00 pm

2 stops23h 00m

George Town Owen Roberts Intl

Wed 11/11

1:10 pm-9:26 am

2 stops23h 16m

$750

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 December, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $666.

Can stopping save me money on Portland to Cayman Islands flights?

You could potentially save up to 15% on your flight if you consider stops on a Portland to Cayman Islands flight.

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 25m

Direct flights

None
The fastest flight from Portland to Cayman Islands takes 10h 25m
There are no direct flights from Portland to Cayman Islands. There are no popular flight routes from Portland to Cayman Islands.
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Frequently asked questions about flying from Portland to the Cayman Islands

  • 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
7.1
11,640 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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