Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Portland to the Cayman Islands from $281

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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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 - 12:30 pmPDX-GCM
19h 05m2 stops
Southwest Logo
1:50 pm - 12:05 amGCM-PDX
13h 15m2 stops
$567Southwest
Find Deal
Fri, Feb 6 - Fri, Feb 13
Multiple Airlines Logo
7:00 am - 11:35 amPDX-GCM
25h 35m1 stop
Multiple Airlines Logo
1:30 pm - 2:40 pmGCM-PDX
28h 10m2 stops
$641Multiple Airlines
Find Deal
Sun, Mar 1 - Tue, Mar 3
Multiple Airlines Logo
7:00 am - 11:35 amPDX-GCM
25h 35m1 stop
Multiple Airlines Logo
11:30 am - 8:23 pmGCM-PDX
11h 53m1 stop
$660Multiple Airlines
Find Deal
Sun, Mar 1 - Tue, Mar 3
American Airlines Logo
10:15 pm - 11:57 amPDX-GCM
10h 42m1 stop
American Airlines Logo
1:20 pm - 11:31 pmGCM-PDX
13h 11m1 stop
$666American Airlines
Find Deal
Fri, Nov 14 - Tue, Nov 18
Delta Logo
5:17 pm - 12:25 pmPDX-GCM
16h 08m2 stops
Delta Logo
1:50 pm - 10:21 pmGCM-PDX
11h 31m1 stop
$671Delta
Find Deal
Fri, Nov 14 - Tue, Nov 18
Multiple Airlines Logo
9:50 am - 1:44 pmPDX-GCM
24h 54m3 stops
Multiple Airlines Logo
1:30 pm - 2:40 pmGCM-PDX
28h 10m2 stops
$696Multiple Airlines
Find Deal
Sun, Mar 1 - Tue, Mar 3
Delta Logo
10:15 am - 12:35 pmPDX-GCM
23h 20m2 stops
Delta Logo
2:00 pm - 9:19 amGCM-PDX
22h 19m2 stops
$714Delta
Find Deal
Sun, Mar 1 - Tue, Mar 3
United Airlines Logo
7:38 pm - 1:45 pmPDX-GCM
15h 07m2 stops
United Airlines Logo
5:45 pm - 10:53 amGCM-PDX
20h 08m3 stops
$781United Airlines
Find Deal
Fri, Nov 14 - Tue, Nov 18
American Airlines Logo
10:45 pm - 8:28 pmPDX-GCM
18h 43m1 stop
American Airlines Logo
9:00 am - 11:31 pmGCM-PDX
17h 31m1 stop
$1,473American Airlines
Find Deal
Thu, Nov 20 - Sat, Nov 29
United Airlines Logo
7:10 pm - 1:45 pmPDX-GCM
39h 35m2 stops
United Airlines Logo
5:30 pm - 9:38 amGCM-PDX
19h 08m2 stops
$1,499United Airlines
Find Deal
Thu, Nov 20 - Sat, Nov 29

American Airlines flights from Portland to Cayman Islands

Our best American Airlines deals on Portland to Cayman Islands flight tickets
American Airlines
Nov 14
PDX10:15 pmPortland
10h 42m
1 stop
GCM11:57 amGeorge Town Owen Roberts Intl
Nov 18
GCM1:20 pmGeorge Town Owen Roberts Intl
13h 11m
1 stop
PDX11:31 pmPortland
$666
Find similar
American Airlines
Nov 20
PDX10:45 pmPortland
18h 43m
1 stop
GCM8:28 pmGeorge Town Owen Roberts Intl
Nov 29
GCM9:00 amGeorge Town Owen Roberts Intl
17h 31m
1 stop
PDX11:31 pmPortland
$1,473
Find similar
American Airlines
Nov 20
PDX10:45 pmPortland
10h 39m
1 stop
GCM12:24 pmGeorge Town Owen Roberts Intl
Nov 29
GCM9:00 amGeorge Town Owen Roberts Intl
17h 31m
1 stop
PDX11:31 pmPortland
$1,550
Find similar

Delta flights from Portland to Cayman Islands

Our best Delta deals on Portland to Cayman Islands flight tickets
Delta
Nov 14
PDX5:17 pmPortland
16h 08m
2 stops
GCM12:25 pmGeorge Town Owen Roberts Intl
Nov 18
GCM1:50 pmGeorge Town Owen Roberts Intl
11h 31m
1 stop
PDX10:21 pmPortland
$671
Find similar
Delta
Mar 1
PDX10:15 amPortland
23h 20m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl
Mar 3
GCM2:00 pmGeorge Town Owen Roberts Intl
22h 19m
2 stops
PDX9:19 amPortland
$714
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 October 16, 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

Fri 2/6

2:25 pm-12:30 pm

2 stops19h 05m

George Town Owen Roberts Intl

Fri 2/13

1:50 pm-12:05 am

2 stops13h 15m

$567

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 3/1

7:00 am-11:35 am

1 stop25h 35m

George Town Owen Roberts Intl

Tue 3/3

1:30 pm-2:40 pm

2 stops28h 10m

$641

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 3/1

7:00 am-11:35 am

1 stop25h 35m

George Town Owen Roberts Intl

Tue 3/3

11:30 am-8:23 pm

1 stop11h 53m

$660

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 11/14

10:15 pm-11:57 am

1 stop10h 42m

George Town Owen Roberts Intl

Tue 11/18

1:20 pm-11:31 pm

1 stop13h 11m

$666

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 11/14

5:17 pm-12:25 pm

2 stops16h 08m

George Town Owen Roberts Intl

Tue 11/18

1:50 pm-10:21 pm

1 stop11h 31m

$671

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 3/1

9:50 am-1:44 pm

3 stops24h 54m

George Town Owen Roberts Intl

Tue 3/3

1:30 pm-2:40 pm

2 stops28h 10m

$696

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Sun 3/1

10:15 am-12:35 pm

2 stops23h 20m

George Town Owen Roberts Intl

Tue 3/3

2:00 pm-9:19 am

2 stops22h 19m

$714

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Fri 11/14

7:38 pm-1:45 pm

2 stops15h 07m

George Town Owen Roberts Intl

Tue 11/18

5:45 pm-10:53 am

3 stops20h 08m

$781

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 11/20

10:45 pm-8:28 pm

1 stop18h 43m

George Town Owen Roberts Intl

Sat 11/29

9:00 am-11:31 pm

1 stop17h 31m

$1,473

PortlandGeorge Town

PDX - GCM

PDXGCM

Portland

Thu 11/20

7:10 pm-1:45 pm

2 stops39h 35m

George Town Owen Roberts Intl

Sat 11/29

5:30 pm-9:38 am

2 stops19h 08m

$1,499

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

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

Direct flights

None
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
8,982 reviews
Search United Airlines flights
American AirlinesPriceFrom $608Free CancellationRating
7.2
11,043 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.

An easier way to manage your Cayman Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 11/15
Sat 11/22
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the Cayman Islands

Popular cities in the Cayman Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to George Townfrom $227
Flights to Cayman Bracfrom $342
Flights to Little Caymanfrom $379