What airlines fly to Caribbean?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Caribbean 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. Keep in mind that there are 5 different airlines that fly to Caribbean 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?

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

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

Prices for flights from Portland Airport to Caribbean were last updated today.

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

There are 6 operators available for flights from Portland Airport to Caribbean as of May 2026.

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

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 Caribbean.

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

The travel and health documents required for your trip to Caribbean can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$172 Cheap Flights from Portland to Caribbean in 2026

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Find the cheapest flights from Portland to Caribbean

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

Our best Southwest deals on Portland to Caribbean 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

Our best American Airlines deals on Portland to Caribbean 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

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?

In general, July is the cheapest month to fly from Portland to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $184. If you don’t want to visit Caribbean in July, then you should wait until August to fly from Portland, when ticket prices are also cheap, with an average price of $185.

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

You are more likely to see cheaper flights to Caribbean from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean 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 from Portland for as low as $507 on momondo.

Can stopping save me money on Portland to Caribbean flights?

You could potentially save up to 15% on your flight if you consider stops on a Portland to Caribbean flight.

Cheap Portland to Caribbean flight deals and tips

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

Fastest flight time	9h 35m
Direct flights	None

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

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

Search flight deals

Frequently asked questions about flying from Portland to Caribbean

When did momondo last update prices for flights from Portland Airport to Caribbean?
Prices for flights from Portland Airport to Caribbean were last updated today.
How many operators does momondo search for flights from Portland Airport to Caribbean?
There are 6 operators available for flights from Portland Airport to Caribbean as of May 2026.
How old do you have to be to fly from Portland Airport to Caribbean?
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 Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents required for your trip to Caribbean can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Portland to Caribbean

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $190	Free Cancellation	Rating 7.9 8,454 reviews	Search Delta flights
United Airlines	PriceFrom $247	Free Cancellation	Rating 7.4 9,729 reviews	Search United Airlines flights
JetBlue	PriceFrom $261	Free Cancellation	Rating 7.1 2,977 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 4,294 reviews	Search Southwest flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Portland to Caribbean. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Portland to Caribbean with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Portland to Caribbean 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 Caribbean right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Portland to Caribbean 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.