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 60% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 6 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?

Frontier, Southwest, and American Airlines 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 December 2025.

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.

$166 Cheap Flights from Portland to Caribbean Islands in 2025/26

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:45 am - 12:40 am

PDX

SJU

13h 55m2 stops

5:40 am - 3:40 pm

SJU

PDX

14h 00m2 stops

$369Southwest

Mon, Jan 19 - Wed, Jan 28

6:45 am - 12:40 am

PDX

SJU

13h 55m2 stops

5:35 am - 5:40 pm

SJU

PDX

16h 05m2 stops

$389Southwest

Thu, Feb 5 - Fri, Feb 6

10:22 pm - 9:33 pm

PDX

SJU

19h 11m1 stop

7:00 am - 6:09 pm

SJU

PDX

15h 09m2 stops

$414American Airlines

Sun, Feb 22 - Tue, Feb 24

5:15 pm - 2:10 pm

PDX

SJU

16h 55m2 stops

7:00 am - 8:32 pm

SJU

PDX

17h 32m2 stops

$419Delta

Mon, Jan 19 - Wed, Jan 28

7:00 am - 9:00 pm

PDX

SJU

10h 00m1 stop

8:10 am - 6:56 pm

SJU

PDX

14h 46m2 stops

$442United Airlines

Thu, Feb 5 - Fri, Feb 6

6:57 pm - 12:34 pm

PDX

SJU

14h 37m2 stops

2:55 pm - 11:02 pm

SJU

PDX

11h 07m1 stop

$446United Airlines

Sun, Apr 19 - Wed, Apr 29

6:00 am - 4:29 pm

PDX

SDQ

31h 29m2 stops

3:35 pm - 8:30 pm

SDQ

PDX

31h 55m1 stop

$478Multiple Airlines

Tue, Mar 10 - Tue, Mar 24

7:10 am - 3:35 pm

PDX

SDQ

28h 25m2 stops

10:19 am - 8:27 pm

SDQ

PDX

14h 08m1 stop

$492Multiple Airlines

Mon, Feb 2 - Fri, Feb 6

9:45 pm - 12:55 pm

PDX

AUA

11h 10m1 stop

2:10 pm - 10:15 pm

AUA

PDX

12h 05m1 stop

$496Delta

Mon, Jan 12 - Thu, Jan 15

11:01 pm - 5:29 pm

PDX

SDQ

14h 28m1 stop

3:00 pm - 11:46 pm

SDQ

PDX

12h 46m1 stop

$541American Airlines

Fri, Jan 30 - Sun, Feb 8

American Airlines flights from Portland to Caribbean Islands

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

American Airlines

Feb 22

PDX10:22 pmPortland

19h 11m

1 stop

SJU9:33 pmSan Juan Luis Munoz Marin Intl

Feb 24

SJU7:00 amSan Juan Luis Munoz Marin Intl

15h 09m

2 stops

PDX6:09 pmPortland

$414

Find similar

American Airlines

Feb 2

PDX6:00 amPortland

11h 39m

1 stop

SJU9:39 pmSan Juan Luis Munoz Marin Intl

Mar 2

SJU7:00 amSan Juan Luis Munoz Marin Intl

20h 59m

1 stop

PDX11:59 pmPortland

$457

Find similar

American Airlines

Apr 1

PDX11:46 amPortland

13h 33m

1 stop

SJU4:19 amSan Juan Luis Munoz Marin Intl

Apr 15

SJU3:50 pmSan Juan Luis Munoz Marin Intl

10h 12m

1 stop

PDX11:02 pmPortland

$467

Find similar

Delta flights from Portland to Caribbean Islands

Our best Delta deals on Portland to Caribbean Islands flight tickets

Delta

Jan 19

PDX9:45 pmPortland

12h 46m

1 stop

SJU2:31 pmSan Juan Luis Munoz Marin Intl

Jan 28

SJU7:00 amSan Juan Luis Munoz Marin Intl

14h 35m

2 stops

PDX5:35 pmPortland

$419

Find similar

Delta

Apr 27

PDX12:55 amPortland

12h 28m

2 stops

SJU4:23 pmSan Juan Luis Munoz Marin Intl

May 5

SJU6:15 amSan Juan Luis Munoz Marin Intl

14h 56m

2 stops

PDX6:11 pmPortland

$472

Find similar

Delta

Jan 17

PDX5:30 amPortland

14h 27m

2 stops

SJU11:57 pmSan Juan Luis Munoz Marin Intl

Jan 23

SJU6:09 amSan Juan Luis Munoz Marin Intl

18h 50m

2 stops

PDX8:59 pmPortland

$482

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Portland to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/19

6:45 am-12:40 am

2 stops13h 55m

San Juan Luis Munoz Marin Intl

Wed 1/28

5:40 am-3:40 pm

2 stops14h 00m

$369

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 2/5

6:45 am-12:40 am

2 stops13h 55m

San Juan Luis Munoz Marin Intl

Fri 2/6

5:35 am-5:40 pm

2 stops16h 05m

$389

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 2/22

10:22 pm-9:33 pm

1 stop19h 11m

San Juan Luis Munoz Marin Intl

Tue 2/24

7:00 am-6:09 pm

2 stops15h 09m

$414

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/19

5:15 pm-2:10 pm

2 stops16h 55m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:00 am-8:32 pm

2 stops17h 32m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 2/5

7:00 am-9:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Fri 2/6

8:10 am-6:56 pm

2 stops14h 46m

$442

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 4/19

6:57 pm-12:34 pm

2 stops14h 37m

San Juan Luis Munoz Marin Intl

Wed 4/29

2:55 pm-11:02 pm

1 stop11h 07m

$446

PortlandSanto Domingo

PDX - SDQ

PDXSDQ

Portland

Tue 3/10

6:00 am-4:29 pm

2 stops31h 29m

Santo Domingo Las Americas

Tue 3/24

3:35 pm-8:30 pm

1 stop31h 55m

$478

PortlandSanto Domingo

PDX - SDQ

PDXSDQ

Portland

Mon 2/2

7:10 am-3:35 pm

2 stops28h 25m

Santo Domingo Las Americas

Fri 2/6

10:19 am-8:27 pm

1 stop14h 08m

$492

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

Mon 1/12

9:45 pm-12:55 pm

1 stop11h 10m

Oranjestad Reina Beatrix

Thu 1/15

2:10 pm-10:15 pm

1 stop12h 05m

$496

PortlandSanto Domingo

PDX - SDQ

PDXSDQ

Portland

Fri 1/30

11:01 pm-5:29 pm

1 stop14h 28m

Santo Domingo Las Americas

Sun 2/8

3:00 pm-11:46 pm

1 stop12h 46m

$541

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 October is, on average, the cheapest month to fly to Caribbean Islands from Portland, with most prices found around $449. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Portland averaging around $485.

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

The cheapest day to depart from Portland to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $454. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $655. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

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

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from Portland to Caribbean Islands in the afternoon for as low as $428. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $602. Of course, these prices can vary depending on the time of year and what airport you fly to.

How far in advance should I book a flight 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 $578 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 $484 on momondo.

Can stopping save me money on Portland to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Portland to Caribbean Islands.

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 13m
Direct flights	None

The fastest flight from Portland to Caribbean Islands takes 9h 13m

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

Search flight deals

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 December 2025.
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 17.66% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 11.98%, Boeing 737 MAX 9 at 8.90%, and Boeing 737-900 Passenger/BBJ3 (winglets) at 8.35%.

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
JetBlue	PriceFrom $185	Free Cancellation	Rating 7.2 2,898 reviews	Search JetBlue flights
Delta	PriceFrom $190	Free Cancellation	Rating 7.9 8,009 reviews	Search Delta flights
Spirit Airlines	PriceFrom $243	Free Cancellation	Rating 6.3 8,159 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $347	Free Cancellation	Rating 7.2 11,044 reviews	Search American Airlines flights
United Airlines	PriceFrom $399	Free Cancellation	Rating 7.4 9,066 reviews	Search United Airlines flights
Southwest	PriceFrom $444	Free Cancellation	Rating 8.0 4,253 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.

An easier way to manage your Caribbean 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

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Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

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Cheap flights from Portland to Caribbean Islands from $166

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 Caribbean Islands departing on 2/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Portland to Caribbean Islands

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

American Airlines flights from Portland to Caribbean Islands

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

Delta flights from Portland to Caribbean Islands

Our best Delta deals on Portland to Caribbean Islands flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Portland to Caribbean Islands that are best for you.

See travel insights to Caribbean Islands from

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

What is the cheapest month to fly to Caribbean Islands?

The month of October is, on average, the cheapest month to fly to Caribbean Islands from Portland, with most prices found around $449. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Portland averaging around $485.

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

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

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

Can stopping save me money on Portland to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Portland to Caribbean Islands.

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

Frontier, Southwest, and American Airlines are the most popular carriers operating from Portland to Caribbean Islands

What airlines fly to Caribbean Islands?

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

Direct flights

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

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

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

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

What is the most popular plane model from Portland to Caribbean Islands?

Best airlines flying from Portland to Caribbean Islands

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

Why use momondo?

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

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

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

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

An easier way to manage your Caribbean 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo