Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Portland, Maine to the Cayman Islands from $438

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, Maine to the Cayman Islands departing on 6/14. 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, Maine to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:36 pm - 11:02 am
PWM
-
GCM
18h 26m
2 stops
American Airlines Logo
5:11 pm - 2:24 pm
GCM
-
PWM
20h 13m
2 stops
$438American Airlines
Sun, Jun 14 - Wed, Jun 17
American Airlines Logo
7:23 pm - 1:10 pm
PWM
-
GCM
18h 47m
2 stops
American Airlines Logo
12:35 pm - 12:38 pm
GCM
-
PWM
23h 03m
1 stop
$449American Airlines
Tue, Apr 21 - Mon, Apr 27
United Airlines Logo
6:18 pm - 12:30 pm
PWM
-
GCM
19h 12m
2 stops
United Airlines Logo
1:35 pm - 2:20 pm
GCM
-
PWM
23h 45m
2 stops
$548United Airlines
Mon, Apr 6 - Mon, Apr 13
United Airlines Logo
6:04 am - 12:45 pm
PWM
-
GCM
7h 41m
1 stop
United Airlines Logo
1:50 pm - 9:40 pm
GCM
-
PWM
30h 50m
1 stop
$552United Airlines
Mon, Apr 6 - Mon, Apr 13
United Airlines Logo
6:04 am - 12:45 pm
PWM
-
GCM
7h 41m
1 stop
United Airlines Logo
1:50 pm - 9:40 pm
GCM
-
PWM
30h 50m
1 stop
$555United Airlines
Tue, Apr 21 - Mon, Apr 27
United Airlines Logo
5:15 am - 12:30 pm
PWM
-
GCM
32h 15m
2 stops
United Airlines Logo
4:10 pm - 9:51 pm
GCM
-
PWM
28h 41m
2 stops
$564United Airlines
Sat, Aug 1 - Sat, Aug 8
United Airlines Logo
9:20 am - 3:05 pm
PWM
-
GCM
6h 45m
1 stop
United Airlines Logo
1:35 pm - 11:59 pm
GCM
-
PWM
33h 24m
2 stops
$569United Airlines
Sat, May 9 - Wed, May 13
United Airlines Logo
3:54 pm - 12:45 pm
PWM
-
GCM
21h 51m
2 stops
United Airlines Logo
4:45 pm - 3:14 pm
GCM
-
PWM
45h 29m
2 stops
$577United Airlines
Sat, Mar 14 - Mon, Mar 16
United Airlines Logo
5:20 am - 12:30 pm
PWM
-
GCM
32h 10m
2 stops
United Airlines Logo
4:45 pm - 9:58 pm
GCM
-
PWM
28h 13m
2 stops
$606United Airlines
Sat, Aug 1 - Sat, Aug 8
American Airlines Logo
5:57 pm - 1:44 pm
PWM
-
GCM
20h 47m
1 stop
American Airlines Logo
2:15 pm - 10:50 pm
GCM
-
PWM
7h 35m
1 stop
$612American Airlines
Sat, Mar 14 - Mon, Mar 16

United Airlines flights from Portland, Maine to Cayman Islands

Our best United Airlines deals on Portland, Maine to Cayman Islands flight tickets
United Airlines
Apr 6
PWM6:18 pmPortland
19h 12m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Apr 13
GCM1:35 pmGeorge Town Owen Roberts Intl
23h 45m
2 stops
PWM2:20 pmPortland
$548
United Airlines
Apr 6
PWM6:04 amPortland
7h 41m
1 stop
GCM12:45 pmGeorge Town Owen Roberts Intl
Apr 13
GCM1:50 pmGeorge Town Owen Roberts Intl
30h 50m
1 stop
PWM9:40 pmPortland
$552
United Airlines
Apr 21
PWM6:04 amPortland
7h 41m
1 stop
GCM12:45 pmGeorge Town Owen Roberts Intl
Apr 27
GCM1:50 pmGeorge Town Owen Roberts Intl
30h 50m
1 stop
PWM9:40 pmPortland
$555

American Airlines flights from Portland, Maine to Cayman Islands

Our best American Airlines deals on Portland, Maine to Cayman Islands flight tickets
American Airlines
Jun 14
PWM5:36 pmPortland
18h 26m
2 stops
GCM11:02 amGeorge Town Owen Roberts Intl
Jun 17
GCM5:11 pmGeorge Town Owen Roberts Intl
20h 13m
2 stops
PWM2:24 pmPortland
$438
American Airlines
Apr 21
PWM7:23 pmPortland
18h 47m
2 stops
GCM1:10 pmGeorge Town Owen Roberts Intl
Apr 27
GCM12:35 pmGeorge Town Owen Roberts Intl
23h 03m
1 stop
PWM12:38 pmPortland
$449
American Airlines
Mar 14
PWM5:57 pmPortland
20h 47m
1 stop
GCM1:44 pmGeorge Town Owen Roberts Intl
Mar 16
GCM2:15 pmGeorge Town Owen Roberts Intl
7h 35m
1 stop
PWM10:50 pmPortland
$612

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine 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 February 23, 2026.
Use the filters below to find and compare flights from Portland, Maine to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sun 6/14

5:36 pm-11:02 am

2 stops18h 26m

George Town Owen Roberts Intl

Wed 6/17

5:11 pm-2:24 pm

2 stops20h 13m

$438

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 4/21

7:23 pm-1:10 pm

2 stops18h 47m

George Town Owen Roberts Intl

Mon 4/27

12:35 pm-12:38 pm

1 stop23h 03m

$449

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Mon 4/6

6:18 pm-12:30 pm

2 stops19h 12m

George Town Owen Roberts Intl

Mon 4/13

1:35 pm-2:20 pm

2 stops23h 45m

$548

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Mon 4/6

6:04 am-12:45 pm

1 stop7h 41m

George Town Owen Roberts Intl

Mon 4/13

1:50 pm-9:40 pm

1 stop30h 50m

$552

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Tue 4/21

6:04 am-12:45 pm

1 stop7h 41m

George Town Owen Roberts Intl

Mon 4/27

1:50 pm-9:40 pm

1 stop30h 50m

$555

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 8/1

5:15 am-12:30 pm

2 stops32h 15m

George Town Owen Roberts Intl

Sat 8/8

4:10 pm-9:51 pm

2 stops28h 41m

$564

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 5/9

9:20 am-3:05 pm

1 stop6h 45m

George Town Owen Roberts Intl

Wed 5/13

1:35 pm-11:59 pm

2 stops33h 24m

$569

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 3/14

3:54 pm-12:45 pm

2 stops21h 51m

George Town Owen Roberts Intl

Mon 3/16

4:45 pm-3:14 pm

2 stops45h 29m

$577

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 8/1

5:20 am-12:30 pm

2 stops32h 10m

George Town Owen Roberts Intl

Sat 8/8

4:45 pm-9:58 pm

2 stops28h 13m

$606

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Sat 3/14

5:57 pm-1:44 pm

1 stop20h 47m

George Town Owen Roberts Intl

Mon 3/16

2:15 pm-10:50 pm

1 stop7h 35m

$612

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, Maine 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 airlines fly to Cayman Islands?

American Airlines, JetBlue and United Airlines are the top three most popular airlines that fly to Cayman Islands from Portland, Maine according to our data. American Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Cayman Islands. Keep in mind that there are 4 different airlines that fly to Cayman Islands on a routine basis, so you have a few additional options to choose from.

Cheap Portland, Maine to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Cayman Islands

Fastest flight time

7h 41m

Direct flights

None
The fastest flight from Portland, Maine to Cayman Islands takes 7h 41m
There are no direct flights from Portland, Maine to Cayman Islands. There are no popular flight routes from Portland, Maine 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 refresh daily.

  • 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 for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Cayman Islands.

  • What documentation or ID do you need to fly to Cayman Islands?

    The necessary travel and health documents for your Cayman Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Portland, Maine to Cayman Islands

Compare and see reviews for airlines that fly from Portland, Maine to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $200Free CancellationRating
7.4
9,342 reviews
Search United Airlines flights
DeltaPriceFrom $480Free CancellationRating
7.9
8,236 reviews
Search Delta flights
American AirlinesPriceFrom $506Free CancellationRating
7.2
11,339 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Cayman Islands?

Finding the right flight to Cayman Islands from Portland is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Cayman Islands quick and easy, saving you time and money.

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?

Yes. momondo can track prices for Portland to Cayman Islands flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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
Wed 3/25
Wed 4/1
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 $223
Flights to Cayman Bracfrom $335
Flights to Little Caymanfrom $342