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Cheap flights from Portland to the Cayman Islands from $218

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 6/2. 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
7:45 pm - 10:00 am
PDX
-
GCM
36h 15m
2 stops
Air Canada Logo
12:25 pm - 9:30 am
GCM
-
PDX
23h 05m
2 stops
$646Air Canada
Thu, Jun 4 - Mon, Jun 8
Southwest Logo
7:50 pm - 11:50 am
PDX
-
GCM
14h 00m
2 stops
Southwest Logo
12:45 pm - 12:30 am
GCM
-
PDX
13h 45m
2 stops
$682Southwest
Wed, Jun 24 - Thu, Jul 2
Southwest Logo
2:50 pm - 12:05 pm
PDX
-
GCM
19h 15m
2 stops
Southwest Logo
1:05 pm - 12:10 am
GCM
-
PDX
13h 05m
2 stops
$687Southwest
Fri, May 15 - Fri, May 22
Southwest Logo
9:20 pm - 11:50 am
PDX
-
GCM
12h 30m
2 stops
Southwest Logo
12:45 pm - 12:05 am
GCM
-
PDX
13h 20m
2 stops
$707Southwest
Tue, Jul 21 - Sun, Jul 26
Air Canada Logo
7:45 pm - 11:25 am
PDX
-
GCM
37h 40m
2 stops
Air Canada Logo
10:40 am - 7:11 pm
GCM
-
PDX
34h 31m
2 stops
$715Air Canada
Sat, Aug 1 - Sat, Aug 8
WestJet Logo
2:30 pm - 12:45 pm
PDX
-
GCM
20h 15m
2 stops
WestJet Logo
1:45 pm - 1:50 pm
GCM
-
PDX
26h 05m
3 stops
$721WestJet
Fri, Jul 24 - Sat, Aug 1
WestJet Logo
2:30 pm - 12:45 pm
PDX
-
GCM
20h 15m
2 stops
WestJet Logo
1:45 pm - 1:50 pm
GCM
-
PDX
26h 05m
2 stops
$725WestJet
Fri, Jul 24 - Sat, Aug 1
Southwest Logo
7:25 pm - 11:50 am
PDX
-
GCM
14h 25m
2 stops
Southwest Logo
11:30 am - 11:55 pm
GCM
-
PDX
14h 25m
2 stops
$727Southwest
Sun, Jul 12 - Sat, Jul 18
Air Canada Logo
7:45 pm - 11:30 am
PDX
-
GCM
13h 45m
2 stops
Air Canada Logo
12:15 pm - 6:30 pm
GCM
-
PDX
32h 15m
2 stops
$734Air Canada
Fri, Oct 16 - Sun, Oct 25
Multiple Airlines Logo
7:45 pm - 11:25 am
PDX
-
GCM
37h 40m
2 stops
Multiple Airlines Logo
8:30 am - 8:50 pm
GCM
-
PDX
14h 20m
1 stop
$754Multiple Airlines
Sat, Aug 1 - Sat, Aug 8

Air Canada flights from Portland to Cayman Islands

Our best Air Canada deals on Portland to Cayman Islands flight tickets
Air Canada
Jun 4
PDX7:45 pmPortland
36h 15m
2 stops
GCM10:00 amGeorge Town Owen Roberts Intl
Jun 8
GCM12:25 pmGeorge Town Owen Roberts Intl
23h 05m
2 stops
PDX9:30 amPortland
$646
Air Canada
Aug 1
PDX7:45 pmPortland
37h 40m
2 stops
GCM11:25 amGeorge Town Owen Roberts Intl
Aug 8
GCM10:40 amGeorge Town Owen Roberts Intl
34h 31m
2 stops
PDX7:11 pmPortland
$715
Air Canada
Oct 16
PDX7:45 pmPortland
13h 45m
2 stops
GCM11:30 amGeorge Town Owen Roberts Intl
Oct 25
GCM12:15 pmGeorge Town Owen Roberts Intl
32h 15m
2 stops
PDX6:30 pmPortland
$734

American Airlines flights from Portland to Cayman Islands

Our best American Airlines deals on Portland to Cayman Islands flight tickets
American Airlines
Jul 12
PDX9:47 pmPortland
11h 38m
1 stop
GCM11:25 amGeorge Town Owen Roberts Intl
Jul 18
GCM12:30 pmGeorge Town Owen Roberts Intl
13h 23m
1 stop
PDX11:53 pmPortland
$797
American Airlines
Jun 7
PDX9:47 pmPortland
11h 43m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
Jun 14
GCM5:12 pmGeorge Town Owen Roberts Intl
19h 57m
2 stops
PDX11:09 amPortland
$799
American Airlines
Jul 24
PDX11:43 pmPortland
8h 40m
1 stop
GCM10:23 amGeorge Town Owen Roberts Intl
Aug 1
GCM2:19 pmGeorge Town Owen Roberts Intl
11h 34m
1 stop
PDX11:53 pmPortland
$830

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 April 24, 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

Thu 6/4

7:45 pm-10:00 am

2 stops36h 15m

George Town Owen Roberts Intl

Mon 6/8

12:25 pm-9:30 am

2 stops23h 05m

$646

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Wed 6/24

7:50 pm-11:50 am

2 stops14h 00m

George Town Owen Roberts Intl

Thu 7/2

12:45 pm-12:30 am

2 stops13h 45m

$682

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 5/15

2:50 pm-12:05 pm

2 stops19h 15m

George Town Owen Roberts Intl

Fri 5/22

1:05 pm-12:10 am

2 stops13h 05m

$687
Quickest round-trip

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 7/21

9:20 pm-11:50 am

2 stops12h 30m

George Town Owen Roberts Intl

Sun 7/26

12:45 pm-12:05 am

2 stops13h 20m

$707

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sat 8/1

7:45 pm-11:25 am

2 stops37h 40m

George Town Owen Roberts Intl

Sat 8/8

10:40 am-7:11 pm

2 stops34h 31m

$715

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 7/24

2:30 pm-12:45 pm

2 stops20h 15m

George Town Owen Roberts Intl

Sat 8/1

1:45 pm-1:50 pm

3 stops26h 05m

$721

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 7/24

2:30 pm-12:45 pm

2 stops20h 15m

George Town Owen Roberts Intl

Sat 8/1

1:45 pm-1:50 pm

2 stops26h 05m

$725

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 7/12

7:25 pm-11:50 am

2 stops14h 25m

George Town Owen Roberts Intl

Sat 7/18

11:30 am-11:55 pm

2 stops14h 25m

$727

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 10/16

7:45 pm-11:30 am

2 stops13h 45m

George Town Owen Roberts Intl

Sun 10/25

12:15 pm-6:30 pm

2 stops32h 15m

$734

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sat 8/1

7:45 pm-11:25 am

2 stops37h 40m

George Town Owen Roberts Intl

Sat 8/8

8:30 am-8:50 pm

1 stop14h 20m

$754

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 April is also cheap. Prices for this month can be found on momondo for an average of $719.

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

12h 30m

Direct flights

None
The fastest flight from Portland to Cayman Islands takes 12h 30m
There are no direct flights from Portland to Cayman Islands. There are no popular flight routes from Portland to Cayman Islands.
Search flight deals

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
11,659 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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