What airlines fly to Caribbean Islands?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Caribbean Islands from Portland according to our data. American Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 5 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Portland to Caribbean Islands?

United Airlines, American Airlines, and Air Canada are the most popular carriers operating from Portland to Caribbean Islands

When did momondo last update prices for flights from Portland Airport to Caribbean Islands?

Prices for flights from Portland Airport to Caribbean Islands are updated daily.

How many operators does momondo search for flights from Portland Airport to Caribbean Islands?

The number of operators available for flights from Portland Airport to Caribbean Islands is 6 as of May 2026.

How old do you have to be to fly from Portland Airport to Caribbean Islands?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$172 Cheap Flights from Portland to Caribbean Islands in 2026

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Find the cheapest flights from Portland to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:35 pm - 11:00 am

PDX

SJU

12h 25m

2 stops

6:30 am - 4:35 pm

SJU

PDX

13h 05m

2 stops

$476Southwest

Mon, Aug 10 - Mon, Aug 17

10:52 pm - 11:43 am

PDX

MBJ

10h 51m

1 stop

4:12 pm - 9:10 am

MBJ

PDX

18h 58m

2 stops

$495United Airlines

Tue, Jun 2 - Fri, Jun 5

5:18 am - 4:13 pm

PDX

MBJ

8h 55m

1 stop

12:47 pm - 9:36 pm

MBJ

PDX

10h 49m

1 stop

$517American Airlines

Wed, Aug 12 - Wed, Aug 19

5:18 am - 4:13 pm

PDX

MBJ

8h 55m

1 stop

2:52 pm - 10:51 am

MBJ

PDX

21h 59m

2 stops

$522American Airlines

Wed, Aug 12 - Wed, Aug 19

3:15 pm - 5:45 pm

PDX

PUJ

23h 30m

2 stops

7:45 pm - 6:31 pm

PUJ

PDX

26h 46m

2 stops

$598Air Canada

Sun, Oct 25 - Sun, Nov 1

7:45 pm - 1:15 pm

PDX

PUJ

38h 30m

2 stops

5:05 pm - 9:25 am

PUJ

PDX

43h 20m

2 stops

$603Air Canada

Fri, Oct 16 - Sat, Oct 24

2:30 pm - 11:40 am

PDX

PUJ

18h 10m

1 stop

2:49 pm - 10:26 pm

PUJ

PDX

10h 37m

1 stop

$610Delta

Fri, Oct 23 - Sat, Oct 31

2:30 pm - 1:44 am

PDX

SDQ

32h 14m

1 stop

3:10 am - 1:10 pm

SDQ

PDX

13h 00m

1 stop

$621JetBlue

Thu, May 28 - Mon, Jun 1

10:35 pm - 6:04 pm

PDX

SDQ

16h 29m

1 stop

7:35 pm - 11:34 am

SDQ

PDX

18h 59m

1 stop

$648Delta

Wed, Jun 10 - Fri, Jun 19

11:27 pm - 2:03 pm

PDX

STT

11h 36m

1 stop

2:58 pm - 1:04 pm

STT

PDX

25h 06m

2 stops

$648JetBlue

Mon, Jul 13 - Tue, Jul 21

Southwest flights from Portland to Caribbean Islands

Our best Southwest deals on Portland to Caribbean Islands flight tickets

Southwest

Aug 20

PDX6:05 amPortland

13h 10m

2 stops

SJU10:15 pmSan Juan Luis Munoz Marin Intl

Aug 24

SJU5:00 amSan Juan Luis Munoz Marin Intl

13h 00m

2 stops

PDX3:00 pmPortland

$466

Southwest

Aug 10

PDX7:35 pmPortland

12h 25m

2 stops

SJU11:00 amSan Juan Luis Munoz Marin Intl

Aug 17

SJU6:30 amSan Juan Luis Munoz Marin Intl

13h 05m

2 stops

PDX4:35 pmPortland

$476

Southwest

Aug 27

PDX10:45 pmPortland

12h 45m

1 stop

SJU2:30 pmSan Juan Luis Munoz Marin Intl

Aug 30

SJU5:30 amSan Juan Luis Munoz Marin Intl

10h 15m

1 stop

PDX12:45 pmPortland

$498

American Airlines flights from Portland to Caribbean Islands

Our best American Airlines deals on Portland to Caribbean Islands flight tickets

American Airlines

Aug 12

PDX5:18 amPortland

8h 55m

1 stop

MBJ4:13 pmMontego Bay Sangster Intl

Aug 19

MBJ12:47 pmMontego Bay Sangster Intl

10h 49m

1 stop

PDX9:36 pmPortland

$517

American Airlines

Aug 12

PDX5:18 amPortland

8h 55m

1 stop

MBJ4:13 pmMontego Bay Sangster Intl

Aug 19

MBJ2:52 pmMontego Bay Sangster Intl

21h 59m

2 stops

PDX10:51 amPortland

$522

American Airlines

Aug 12

PDX11:20 pmPortland

20h 47m

1 stop

SJU11:07 pmSan Juan Luis Munoz Marin Intl

Aug 20

SJU12:59 amSan Juan Luis Munoz Marin Intl

13h 40m

1 stop

PDX11:39 amPortland

$535

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 8/10

7:35 pm-11:00 am

2 stops12h 25m

San Juan Luis Munoz Marin Intl

Mon 8/17

6:30 am-4:35 pm

2 stops13h 05m

$476

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Tue 6/2

10:52 pm-11:43 am

1 stop10h 51m

Montego Bay Sangster Intl

Fri 6/5

4:12 pm-9:10 am

2 stops18h 58m

$495

Quickest round-trip

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Wed 8/12

5:18 am-4:13 pm

1 stop8h 55m

Montego Bay Sangster Intl

Wed 8/19

12:47 pm-9:36 pm

1 stop10h 49m

$517

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Wed 8/12

5:18 am-4:13 pm

1 stop8h 55m

Montego Bay Sangster Intl

Wed 8/19

2:52 pm-10:51 am

2 stops21h 59m

$522

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Sun 10/25

3:15 pm-5:45 pm

2 stops23h 30m

Punta Cana

Sun 11/1

7:45 pm-6:31 pm

2 stops26h 46m

$598

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Fri 10/16

7:45 pm-1:15 pm

2 stops38h 30m

Punta Cana

Sat 10/24

5:05 pm-9:25 am

2 stops43h 20m

$603

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Fri 10/23

2:30 pm-11:40 am

1 stop18h 10m

Punta Cana

Sat 10/31

2:49 pm-10:26 pm

1 stop10h 37m

$610

PortlandSanto Domingo

PDX - SDQ

PDXSDQ

Portland

Thu 5/28

2:30 pm-1:44 am

1 stop32h 14m

Santo Domingo Las Americas

Mon 6/1

3:10 am-1:10 pm

1 stop13h 00m

$621

PortlandSanto Domingo

PDX - SDQ

PDXSDQ

Portland

Wed 6/10

10:35 pm-6:04 pm

1 stop16h 29m

Santo Domingo Las Americas

Fri 6/19

7:35 pm-11:34 am

1 stop18h 59m

$648

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Mon 7/13

11:27 pm-2:03 pm

1 stop11h 36m

Saint Thomas Island Cyril E King

Tue 7/21

2:58 pm-1:04 pm

2 stops25h 06m

$648

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Portland to Caribbean 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

Prices

Airlines

What is the cheapest month to fly to Caribbean Islands?

The month of July is, on average, the cheapest month to fly to Caribbean Islands from Portland, with most prices found around $184. The month of August is another great option to travel to Caribbean Islands, with average flight prices from Portland averaging around $191.

How far in advance should I book a flight from Portland to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $584 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Portland for as low as $507 on momondo.

Cheap Portland to Caribbean Islands flight deals and tips

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

Fastest flight time	9h 35m
Direct flights	None

The fastest flight from Portland to Caribbean Islands takes 9h 35m

There are no direct flights from Portland to Caribbean Islands. There are no popular flight routes from Portland to Caribbean Islands.

Search flight deals

Frequently asked questions about flying from Portland to Caribbean Islands

When did momondo last update prices for flights from Portland Airport to Caribbean Islands?
Prices for flights from Portland Airport to Caribbean Islands are updated daily.
How many operators does momondo search for flights from Portland Airport to Caribbean Islands?
The number of operators available for flights from Portland Airport to Caribbean Islands is 6 as of May 2026.
How old do you have to be to fly from Portland Airport to Caribbean Islands?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Portland to Caribbean Islands?
momondo data reveals that the most frequently booked plane model on the route from Portland to Caribbean Islands is Boeing 737-800 Passenger/BBJ2 (winglets), representing 20.83% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 13.57%, Boeing 737-800 at 8.93%, and Airbus A321neo at 8.64%.

Best airlines flying from Portland to Caribbean Islands

Compare and see reviews for airlines that fly from Portland to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $190	Free Cancellation	Rating 7.9 8,453 reviews	Search Delta flights
United Airlines	PriceFrom $247	Free Cancellation	Rating 7.4 9,720 reviews	Search United Airlines flights
JetBlue	PriceFrom $261	Free Cancellation	Rating 7.1 2,974 reviews	Search JetBlue flights
American Airlines	PriceFrom $396	Free Cancellation	Rating 7.1 11,662 reviews	Search American Airlines flights
Southwest	PriceFrom $408	Free Cancellation	Rating 8.0 4,299 reviews	Search Southwest flights

Why use momondo?

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

It is quick and easy to find Portland to Caribbean 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 Caribbean Islands that suits you.

Can I find flights from Portland to Caribbean Islands with flexible booking policies on momondo?

All flight searches from Portland to Caribbean Islands on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Portland to Caribbean Islands?

momondo helps you find the best flight between Portland and Caribbean Islands by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Portland to Caribbean Islands right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Portland to Caribbean Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean Islands and let you know when they change.