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Cheap flights from Portland to the Cayman Islands from $260

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 8/29. 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
7:45 pm - 11:30 am
PDX
-
GCM
37h 45m
2 stops
Air Canada Logo
12:25 pm - 6:31 pm
GCM
-
PDX
32h 06m
2 stops
$666Air Canada
Tue, Oct 13 - Sat, Oct 24
Southwest Logo
1:40 pm - 12:35 pm
PDX
-
GCM
19h 55m
2 stops
Southwest Logo
1:30 pm - 10:20 am
GCM
-
PDX
23h 50m
2 stops
$687Southwest
Sat, Dec 12 - Thu, Dec 17
Multiple Airlines Logo
3:15 pm - 12:10 pm
PDX
-
GCM
17h 55m
2 stops
Multiple Airlines Logo
7:00 am - 8:50 pm
GCM
-
PDX
16h 50m
1 stop
$727Multiple Airlines
Sat, Dec 12 - Thu, Dec 17
Air Canada Logo
3:15 pm - 12:10 pm
PDX
-
GCM
17h 55m
2 stops
Air Canada Logo
1:10 pm - 2:41 pm
GCM
-
PDX
28h 31m
2 stops
$734Air Canada
Mon, Jan 11 - Thu, Jan 14
Air Canada Logo
7:10 pm - 12:10 pm
PDX
-
GCM
38h 00m
2 stops
Air Canada Logo
1:10 pm - 2:41 pm
GCM
-
PDX
28h 31m
2 stops
$738Air Canada
Mon, Jan 11 - Thu, Jan 14
Air Canada Logo
3:15 pm - 12:10 pm
PDX
-
GCM
17h 55m
2 stops
Air Canada Logo
1:10 pm - 2:41 pm
GCM
-
PDX
28h 31m
2 stops
$762Air Canada
Mon, Jan 11 - Thu, Jan 14
Multiple Airlines Logo
6:04 pm - 7:10 pm
PDX
-
GCM
23h 06m
1 stop
Multiple Airlines Logo
4:45 pm - 5:11 pm
GCM
-
PDX
26h 26m
2 stops
$780Multiple Airlines
Fri, Aug 14 - Thu, Aug 20
American Airlines Logo
10:45 pm - 12:10 pm
PDX
-
GCM
10h 25m
1 stop
American Airlines Logo
12:55 pm - 9:19 pm
GCM
-
PDX
11h 24m
1 stop
$781American Airlines
Sat, Dec 12 - Thu, Dec 17
American Airlines Logo
3:00 pm - 11:00 am
PDX
-
GCM
18h 00m
2 stops
American Airlines Logo
12:00 pm - 11:09 pm
GCM
-
PDX
13h 09m
2 stops
$786American Airlines
Mon, Aug 17 - Mon, Aug 24
American Airlines Logo
12:48 pm - 11:27 am
PDX
-
GCM
20h 39m
1 stop
American Airlines Logo
12:30 pm - 11:09 pm
GCM
-
PDX
12h 39m
2 stops
$806American Airlines
Tue, Sep 1 - Tue, Sep 8

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Delta flights from Portland to Cayman Islands

Our best Delta deals on Portland to Cayman Islands flight tickets
Delta
Aug 14
PDX10:55 pmPortland
10h 44m
1 stop
GCM11:39 amGeorge Town Owen Roberts Intl
Aug 20
GCM1:04 pmGeorge Town Owen Roberts Intl
10h 40m
1 stop
PDX9:44 pmPortland
$837
Delta
Aug 15
PDX5:35 pmPortland
16h 04m
2 stops
GCM11:39 amGeorge Town Owen Roberts Intl
Aug 20
GCM1:04 pmGeorge Town Owen Roberts Intl
23h 22m
2 stops
PDX10:26 amPortland
$842
Delta
Aug 18
PDX10:55 pmPortland
10h 44m
1 stop
GCM11:39 amGeorge Town Owen Roberts Intl
Aug 24
GCM1:04 pmGeorge Town Owen Roberts Intl
10h 40m
1 stop
PDX9:44 pmPortland
$884

United Airlines flights from Portland to Cayman Islands

Our best United Airlines deals on Portland to Cayman Islands flight tickets
United Airlines
Jan 11
PDX10:56 pmPortland
11h 19m
1 stop
GCM1:15 pmGeorge Town Owen Roberts Intl
Jan 14
GCM2:50 pmGeorge Town Owen Roberts Intl
11h 22m
1 stop
PDX11:12 pmPortland
$957
United Airlines
Jan 11
PDX1:39 pmPortland
20h 36m
2 stops
GCM1:15 pmGeorge Town Owen Roberts Intl
Jan 14
GCM2:50 pmGeorge Town Owen Roberts Intl
11h 22m
1 stop
PDX11:12 pmPortland
$962
United Airlines
Jul 26
PDX5:15 amPortland
29h 15m
3 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Jul 30
GCM1:35 pmGeorge Town Owen Roberts Intl
22h 45m
2 stops
PDX10:20 amPortland
$1,096

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 July 22, 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

Tue 10/13

7:45 pm-11:30 am

2 stops37h 45m

George Town Owen Roberts Intl

Sat 10/24

12:25 pm-6:31 pm

2 stops32h 06m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sat 12/12

1:40 pm-12:35 pm

2 stops19h 55m

George Town Owen Roberts Intl

Thu 12/17

1:30 pm-10:20 am

2 stops23h 50m

$687

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sat 12/12

3:15 pm-12:10 pm

2 stops17h 55m

George Town Owen Roberts Intl

Thu 12/17

7:00 am-8:50 pm

1 stop16h 50m

$727

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 1/11

3:15 pm-12:10 pm

2 stops17h 55m

George Town Owen Roberts Intl

Thu 1/14

1:10 pm-2:41 pm

2 stops28h 31m

$734

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 1/11

7:10 pm-12:10 pm

2 stops38h 00m

George Town Owen Roberts Intl

Thu 1/14

1:10 pm-2:41 pm

2 stops28h 31m

$738

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 1/11

3:15 pm-12:10 pm

2 stops17h 55m

George Town Owen Roberts Intl

Thu 1/14

1:10 pm-2:41 pm

2 stops28h 31m

$762

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 8/14

6:04 pm-7:10 pm

1 stop23h 06m

George Town Owen Roberts Intl

Thu 8/20

4:45 pm-5:11 pm

2 stops26h 26m

$780
Quickest round-trip

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sat 12/12

10:45 pm-12:10 pm

1 stop10h 25m

George Town Owen Roberts Intl

Thu 12/17

12:55 pm-9:19 pm

1 stop11h 24m

$781

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 8/17

3:00 pm-11:00 am

2 stops18h 00m

George Town Owen Roberts Intl

Mon 8/24

12:00 pm-11:09 pm

2 stops13h 09m

$786

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 9/1

12:48 pm-11:27 am

1 stop20h 39m

George Town Owen Roberts Intl

Tue 9/8

12:30 pm-11:09 pm

2 stops12h 39m

$806

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 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 September is also cheap. Prices for this month can be found on momondo for an average of $670.

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 36m

Direct flights

None
The fastest flight from Portland to Cayman Islands takes 10h 36m
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
11,834 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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