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Cheap flights from Portland to the Cayman Islands from $230

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 1/5. 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.
Southwest Logo
2:25 pm - 12:55 pmPDX-GCM
19h 30m2 stops
Southwest Logo
1:50 pm - 12:45 amGCM-PDX
13h 55m2 stops
$469Southwest
Find Deal
Tue, Jan 13 - Thu, Feb 12
Southwest Logo
2:25 pm - 12:55 pmPDX-GCM
19h 30m2 stops
Southwest Logo
1:50 pm - 10:30 pmGCM-PDX
11h 40m2 stops
$509Southwest
Find Deal
Thu, Jan 8 - Thu, Feb 5
Multiple Airlines Logo
7:00 am - 4:05 pmPDX-GCM
30h 05m1 stop
Multiple Airlines Logo
2:40 pm - 11:46 pmGCM-PDX
12h 06m2 stops
$520Multiple Airlines
Find Deal
Tue, Jan 13 - Thu, Feb 12
Multiple Airlines Logo
7:00 am - 4:05 pmPDX-GCM
30h 05m1 stop
Multiple Airlines Logo
4:45 pm - 8:44 pmGCM-PDX
30h 59m1 stop
$530Multiple Airlines
Find Deal
Tue, Jan 13 - Thu, Feb 12
Multiple Airlines Logo
7:00 am - 9:15 pmPDX-GCM
11h 15m1 stop
Multiple Airlines Logo
7:00 am - 8:27 pmGCM-PDX
16h 27m1 stop
$545Multiple Airlines
Find Deal
Thu, Jan 8 - Thu, Feb 5
Multiple Airlines Logo
1:38 pm - 9:15 pmPDX-GCM
28h 37m2 stops
Multiple Airlines Logo
11:30 am - 8:27 pmGCM-PDX
11h 57m1 stop
$551Multiple Airlines
Find Deal
Sun, Jan 11 - Tue, Feb 10
Multiple Airlines Logo
7:00 am - 11:35 amPDX-GCM
25h 35m1 stop
Multiple Airlines Logo
11:30 am - 8:27 pmGCM-PDX
11h 57m1 stop
$561Multiple Airlines
Find Deal
Sun, Jan 11 - Tue, Feb 10
Multiple Airlines Logo
7:00 am - 9:15 pmPDX-GCM
11h 15m1 stop
Multiple Airlines Logo
1:30 pm - 2:40 pmGCM-PDX
28h 10m2 stops
$578Multiple Airlines
Find Deal
Thu, Jan 8 - Thu, Feb 5
Air Canada Logo
3:15 pm - 12:25 pmPDX-GCM
42h 10m2 stops
Air Canada Logo
1:30 pm - 2:40 pmGCM-PDX
28h 10m2 stops
$613Air Canada
Find Deal
Sun, Jan 11 - Tue, Feb 10
Air Canada Logo
9:50 am - 12:25 pmPDX-GCM
23h 35m2 stops
Air Canada Logo
1:30 pm - 2:40 pmGCM-PDX
28h 10m2 stops
$615Air Canada
Find Deal
Mon, Feb 23 - Thu, Feb 26

Southwest flights from Portland to Cayman Islands

Our best Southwest deals on Portland to Cayman Islands flight tickets
Southwest
Jan 13
PDX2:25 pmPortland
19h 30m
2 stops
GCM12:55 pmGeorge Town Owen Roberts Intl
Feb 12
GCM1:50 pmGeorge Town Owen Roberts Intl
13h 55m
2 stops
PDX12:45 amPortland
$469
Find similar
Southwest
Jan 8
PDX2:25 pmPortland
19h 30m
2 stops
GCM12:55 pmGeorge Town Owen Roberts Intl
Feb 5
GCM1:50 pmGeorge Town Owen Roberts Intl
11h 40m
2 stops
PDX10:30 pmPortland
$509
Find similar

Air Canada flights from Portland to Cayman Islands

Our best Air Canada deals on Portland to Cayman Islands flight tickets
Air Canada
Jan 11
PDX3:15 pmPortland
42h 10m
2 stops
GCM12:25 pmGeorge Town Owen Roberts Intl
Feb 10
GCM1:30 pmGeorge Town Owen Roberts Intl
28h 10m
2 stops
PDX2:40 pmPortland
$613
Find similar
Air Canada
Feb 23
PDX9:50 amPortland
23h 35m
2 stops
GCM12:25 pmGeorge Town Owen Roberts Intl
Feb 26
GCM1:30 pmGeorge Town Owen Roberts Intl
28h 10m
2 stops
PDX2:40 pmPortland
$615
Find similar
Air Canada
May 20
PDX7:40 pmPortland
14h 15m
2 stops
GCM11:55 amGeorge Town Owen Roberts Intl
May 25
GCM12:50 pmGeorge Town Owen Roberts Intl
31h 56m
2 stops
PDX6:46 pmPortland
$621
Find similar

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 December 3, 2025.
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

Tue 1/13

2:25 pm-12:55 pm

2 stops19h 30m

George Town Owen Roberts Intl

Thu 2/12

1:50 pm-12:45 am

2 stops13h 55m

$469

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 1/8

2:25 pm-12:55 pm

2 stops19h 30m

George Town Owen Roberts Intl

Thu 2/5

1:50 pm-10:30 pm

2 stops11h 40m

$509

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 1/13

7:00 am-4:05 pm

1 stop30h 05m

George Town Owen Roberts Intl

Thu 2/12

2:40 pm-11:46 pm

2 stops12h 06m

$520

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Tue 1/13

7:00 am-4:05 pm

1 stop30h 05m

George Town Owen Roberts Intl

Thu 2/12

4:45 pm-8:44 pm

1 stop30h 59m

$530

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 1/8

7:00 am-9:15 pm

1 stop11h 15m

George Town Owen Roberts Intl

Thu 2/5

7:00 am-8:27 pm

1 stop16h 27m

$545

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 1/11

1:38 pm-9:15 pm

2 stops28h 37m

George Town Owen Roberts Intl

Tue 2/10

11:30 am-8:27 pm

1 stop11h 57m

$551

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 1/11

7:00 am-11:35 am

1 stop25h 35m

George Town Owen Roberts Intl

Tue 2/10

11:30 am-8:27 pm

1 stop11h 57m

$561

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 1/8

7:00 am-9:15 pm

1 stop11h 15m

George Town Owen Roberts Intl

Thu 2/5

1:30 pm-2:40 pm

2 stops28h 10m

$578

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 1/11

3:15 pm-12:25 pm

2 stops42h 10m

George Town Owen Roberts Intl

Tue 2/10

1:30 pm-2:40 pm

2 stops28h 10m

$613

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Mon 2/23

9:50 am-12:25 pm

2 stops23h 35m

George Town Owen Roberts Intl

Thu 2/26

1:30 pm-2:40 pm

2 stops28h 10m

$615

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 July is also cheap. Prices for this month can be found on momondo for an average of $667.

What is the cheapest day to depart on your flight to Cayman Islands?

Our data shows that Tuesday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $624. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Saturday is $746.

What is the cheapest time of day to depart on your flight to Cayman Islands?

According to our data, the cheapest time of day to fly to Cayman Islands is in the afternoon. momondo users have found flights departing from Portland to Cayman Islands in the afternoon for as low as $557. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $833 on average. Flights to Cayman Islands from Portland at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

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 12m

Direct flights

None
The fastest flight from Portland to Cayman Islands takes 10h 12m
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
United AirlinesPriceFrom $578Free CancellationRating
7.4
9,065 reviews
Search United Airlines flights
American AirlinesPriceFrom $609Free CancellationRating
7.2
11,046 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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