What airlines fly to Caribbean Islands?

American Airlines, Delta and United Airlines 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 61% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 7 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?

American Airlines, Delta, and Southwest 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 7 as of September 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.

$191 Cheap Flights from Portland to Caribbean Islands in 2025/26

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Find the cheapest flights from Portland to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

3:26 pm - 4:10 pmPDX-SJU

20h 44m2 stops

1:59 am - 11:56 amSJU-PDX

13h 57m2 stops

$403Frontier

Find Deal

Sun, Nov 9 - Wed, Nov 12

3:26 pm - 4:10 pmPDX-SJU

20h 44m2 stops

10:39 pm - 11:56 amSJU-PDX

17h 17m2 stops

$415Frontier

Find Deal

Sun, Nov 9 - Thu, Nov 13

6:04 am - 11:49 pmPDX-SJU

13h 45m1 stop

2:12 pm - 9:35 pmSJU-PDX

11h 23m1 stop

$419Delta

Find Deal

Mon, Jan 12 - Wed, Jan 14

7:58 am - 4:55 amPDX-SJU

16h 57m1 stop

7:20 am - 8:24 pmSJU-PDX

17h 04m1 stop

$444American Airlines

Find Deal

Sun, Feb 15 - Sat, Feb 21

7:00 am - 9:00 pmPDX-SJU

10h 00m1 stop

2:05 am - 2:47 pmSJU-PDX

16h 42m2 stops

$447United Airlines

Find Deal

Sun, Dec 7 - Fri, Dec 12

11:59 pm - 3:40 pmPDX-SJU

11h 41m1 stop

3:46 pm - 10:57 pmSJU-PDX

11h 11m1 stop

$457United Airlines

Find Deal

Tue, Dec 2 - Fri, Dec 12

6:15 am - 10:05 pmPDX-SJU

11h 50m2 stops

8:55 am - 7:20 pmSJU-PDX

14h 25m2 stops

$464Southwest

Find Deal

Thu, Dec 4 - Tue, Dec 9

12:35 am - 12:59 amPDX-STI

20h 24m2 stops

8:57 pm - 3:33 pmSTI-PDX

22h 36m2 stops

$472Delta

Find Deal

Sun, Nov 23 - Mon, Dec 8

11:59 pm - 3:54 pmPDX-SJU

12h 55m2 stops

3:00 pm - 9:31 amSJU-PDX

21h 31m1 stop

$473American Airlines

Find Deal

Mon, Oct 13 - Fri, Oct 17

6:30 am - 11:10 pmPDX-SJU

12h 40m2 stops

6:10 am - 3:40 pmSJU-PDX

13h 30m2 stops

$508Southwest

Find Deal

Tue, Jan 13 - Sun, Jan 18

Frontier flights from Portland to Caribbean Islands

Our best Frontier deals on Portland to Caribbean Islands flight tickets

Frontier

Nov 9

PDX3:26 pmPortland

20h 44m

2 stops

SJU4:10 pmSan Juan Luis Munoz Marin Intl

Nov 12

SJU1:59 amSan Juan Luis Munoz Marin Intl

13h 57m

2 stops

PDX11:56 amPortland

$403

Find similar

Frontier

Nov 9

PDX3:26 pmPortland

20h 44m

2 stops

SJU4:10 pmSan Juan Luis Munoz Marin Intl

Nov 13

SJU10:39 pmSan Juan Luis Munoz Marin Intl

17h 17m

2 stops

PDX11:56 amPortland

$415

Find similar

Frontier

Oct 22

PDX12:43 pmPortland

19h 18m

2 stops

SJU11:01 amSan Juan Luis Munoz Marin Intl

Oct 31

SJU10:39 pmSan Juan Luis Munoz Marin Intl

16h 17m

2 stops

PDX11:56 amPortland

$426

Find similar

Delta flights from Portland to Caribbean Islands

Our best Delta deals on Portland to Caribbean Islands flight tickets

Delta

Jan 12

PDX6:04 amPortland

13h 45m

1 stop

SJU11:49 pmSan Juan Luis Munoz Marin Intl

Jan 14

SJU2:12 pmSan Juan Luis Munoz Marin Intl

11h 23m

1 stop

PDX9:35 pmPortland

$419

Find similar

Delta

Jan 11

PDX7:45 pmPortland

13h 22m

2 stops

SJU1:07 pmSan Juan Luis Munoz Marin Intl

Jan 16

SJU6:15 amSan Juan Luis Munoz Marin Intl

18h 32m

2 stops

PDX8:47 pmPortland

$472

Find similar

Delta

Jan 1

PDX5:20 amPortland

17h 01m

2 stops

SJU2:21 amSan Juan Luis Munoz Marin Intl

Jan 16

SJU6:15 amSan Juan Luis Munoz Marin Intl

18h 32m

2 stops

PDX8:47 pmPortland

$477

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

Sun 11/9

3:26 pm-4:10 pm

2 stops20h 44m

San Juan Luis Munoz Marin Intl

Wed 11/12

1:59 am-11:56 am

2 stops13h 57m

$403

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 11/9

3:26 pm-4:10 pm

2 stops20h 44m

San Juan Luis Munoz Marin Intl

Thu 11/13

10:39 pm-11:56 am

2 stops17h 17m

$415

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/12

6:04 am-11:49 pm

1 stop13h 45m

San Juan Luis Munoz Marin Intl

Wed 1/14

2:12 pm-9:35 pm

1 stop11h 23m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 2/15

7:58 am-4:55 am

1 stop16h 57m

San Juan Luis Munoz Marin Intl

Sat 2/21

7:20 am-8:24 pm

1 stop17h 04m

$444

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 12/7

7:00 am-9:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Fri 12/12

2:05 am-2:47 pm

2 stops16h 42m

$447

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 12/2

11:59 pm-3:40 pm

1 stop11h 41m

San Juan Luis Munoz Marin Intl

Fri 12/12

3:46 pm-10:57 pm

1 stop11h 11m

$457

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 12/4

6:15 am-10:05 pm

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Tue 12/9

8:55 am-7:20 pm

2 stops14h 25m

$464

PortlandSantiago de los Caballeros

PDX - STI

PDXSTI

Portland

Sun 11/23

12:35 am-12:59 am

2 stops20h 24m

Santiago de los Caballeros

Mon 12/8

8:57 pm-3:33 pm

2 stops22h 36m

$472

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 10/13

11:59 pm-3:54 pm

2 stops12h 55m

San Juan Luis Munoz Marin Intl

Fri 10/17

3:00 pm-9:31 am

1 stop21h 31m

$473

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 1/13

6:30 am-11:10 pm

2 stops12h 40m

San Juan Luis Munoz Marin Intl

Sun 1/18

6:10 am-3:40 pm

2 stops13h 30m

$508

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 $476. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Portland averaging around $481.

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 $574 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 $438 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

Direct flights	None

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 7 as of September 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 13.18% of all bookings. The subsequent popular models are Boeing 737 MAX 9 at 10.87%, Boeing 737-900 Passenger/BBJ3 (winglets) at 10.15%, and Boeing 737 MAX 8 at 9.45%.

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 2,911 reviews	Search JetBlue flights
Delta	PriceFrom $190	Free Cancellation	Rating 7.9 7,971 reviews	Search Delta flights
Spirit Airlines	PriceFrom $248	Free Cancellation	Rating 6.3 8,031 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $341	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $399	Free Cancellation	Rating 7.4 8,922 reviews	Search United Airlines flights
Southwest	PriceFrom $450	Free Cancellation	Rating 8.0 4,244 reviews	Search Southwest flights
Alaska Airlines	PriceFrom $454	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines 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.

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Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

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Flights to Romefrom $305

Flights to Miamifrom $49

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Cheap flights from Portland to Caribbean Islands from $191

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 1/3. 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

Frontier flights from Portland to Caribbean Islands

Our best Frontier 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 $476. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Portland averaging around $481.

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?

American Airlines, Delta, and Southwest 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

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