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

United Airlines, Delta, and Spirit Airlines are the most popular carriers operating from Portland to Caribbean Islands

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.

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 July 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.

$200 Cheap Flights from Portland to Caribbean Islands in 2025

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Find the cheapest flights from Portland to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

6:00 am - 10:30 pmPDX-SJU

13h 30m2 stops

5:50 am - 4:00 pmSJU-PDX

13h 10m1 stop

$389Southwest

Find Deal

Tue, Sep 9 - Fri, Sep 19

8:04 pm - 12:43 amPDX-SJU

25h 39m3 stops

2:48 pm - 7:04 pmSJU-PDX

31h 16m3 stops

$393Spirit Airlines

Find Deal

Wed, Oct 15 - Thu, Oct 30

5:10 pm - 12:13 pmPDX-SJU

16h 03m2 stops

1:32 pm - 11:52 pmSJU-PDX

13h 20m2 stops

$399Delta

Find Deal

Tue, Sep 16 - Wed, Oct 1

5:30 am - 11:51 pmPDX-SJU

15h 21m2 stops

7:00 am - 11:52 pmSJU-PDX

19h 52m2 stops

$409Delta

Find Deal

Tue, Sep 9 - Wed, Sep 17

11:58 pm - 3:40 pmPDX-SJU

12h 42m1 stop

5:50 am - 11:16 pmSJU-PDX

21h 26m1 stop

$419American Airlines

Find Deal

Thu, Oct 30 - Sun, Dec 7

7:04 am - 8:38 pmPDX-SJU

10h 34m1 stop

1:25 pm - 9:37 pmSJU-PDX

11h 12m1 stop

$428United Airlines

Find Deal

Tue, Sep 9 - Fri, Sep 19

10:17 pm - 12:00 pmPDX-SJU

10h 43m1 stop

1:05 am - 8:53 amSJU-PDX

10h 48m1 stop

$429United Airlines

Find Deal

Fri, Oct 10 - Wed, Oct 15

9:56 pm - 1:05 pmPDX-NAS

12h 09m1 stop

2:09 pm - 8:37 pmNAS-PDX

9h 28m1 stop

$439American Airlines

Find Deal

Sat, Sep 13 - Sat, Sep 20

10:17 am - 8:56 pmPDX-SJU

31h 39m3 stops

3:19 pm - 7:23 pmSJU-PDX

31h 04m3 stops

$448

Find Deal

Fri, Sep 5 - Tue, Sep 9

12:07 pm - 8:56 pmPDX-SJU

29h 49m3 stops

3:19 pm - 5:24 pmSJU-PDX

29h 05m3 stops

$459

Find Deal

Mon, Sep 8 - Sat, Sep 13

Delta flights from Portland to Caribbean Islands

Our best Delta deals on Portland to Caribbean Islands flight tickets

Delta

Sep 16

PDX5:10 pmPortland

16h 03m

2 stops

SJU12:13 pmSan Juan Luis Munoz Marin Intl

Oct 1

SJU1:32 pmSan Juan Luis Munoz Marin Intl

13h 20m

2 stops

PDX11:52 pmPortland

$399

Find similar

Delta

Sep 9

PDX5:30 amPortland

15h 21m

2 stops

SJU11:51 pmSan Juan Luis Munoz Marin Intl

Sep 17

SJU7:00 amSan Juan Luis Munoz Marin Intl

19h 52m

2 stops

PDX11:52 pmPortland

$409

Find similar

Delta

Sep 8

PDX5:45 pmPortland

15h 33m

2 stops

SJU12:18 pmSan Juan Luis Munoz Marin Intl

Sep 12

SJU2:15 pmSan Juan Luis Munoz Marin Intl

10h 22m

1 stop

PDX9:37 pmPortland

$454

Find similar

United Airlines flights from Portland to Caribbean Islands

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

United Airlines

Sep 9

PDX7:04 amPortland

10h 34m

1 stop

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Sep 19

SJU1:25 pmSan Juan Luis Munoz Marin Intl

11h 12m

1 stop

PDX9:37 pmPortland

$428

Find similar

United Airlines

Oct 10

PDX10:17 pmPortland

10h 43m

1 stop

SJU12:00 pmSan Juan Luis Munoz Marin Intl

Oct 15

SJU1:05 amSan Juan Luis Munoz Marin Intl

10h 48m

1 stop

PDX8:53 amPortland

$429

Find similar

United Airlines

Nov 14

PDX8:30 amPortland

12h 06m

2 stops

SJU12:36 amSan Juan Luis Munoz Marin Intl

Dec 12

SJU8:10 amSan Juan Luis Munoz Marin Intl

13h 56m

2 stops

PDX6:06 pmPortland

$440

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

Tue 9/9

6:00 am-10:30 pm

2 stops13h 30m

San Juan Luis Munoz Marin Intl

Fri 9/19

5:50 am-4:00 pm

1 stop13h 10m

$389

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 10/15

8:04 pm-12:43 am

3 stops25h 39m

San Juan Luis Munoz Marin Intl

Thu 10/30

2:48 pm-7:04 pm

3 stops31h 16m

$393

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 9/16

5:10 pm-12:13 pm

2 stops16h 03m

San Juan Luis Munoz Marin Intl

Wed 10/1

1:32 pm-11:52 pm

2 stops13h 20m

$399

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 9/9

5:30 am-11:51 pm

2 stops15h 21m

San Juan Luis Munoz Marin Intl

Wed 9/17

7:00 am-11:52 pm

2 stops19h 52m

$409

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 10/30

11:58 pm-3:40 pm

1 stop12h 42m

San Juan Luis Munoz Marin Intl

Sun 12/7

5:50 am-11:16 pm

1 stop21h 26m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 9/9

7:04 am-8:38 pm

1 stop10h 34m

San Juan Luis Munoz Marin Intl

Fri 9/19

1:25 pm-9:37 pm

1 stop11h 12m

$428

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 10/10

10:17 pm-12:00 pm

1 stop10h 43m

San Juan Luis Munoz Marin Intl

Wed 10/15

1:05 am-8:53 am

1 stop10h 48m

$429

PortlandNassau

PDX - NAS

PDXNAS

Portland

Sat 9/13

9:56 pm-1:05 pm

1 stop12h 09m

Nassau Intl

Sat 9/20

2:09 pm-8:37 pm

1 stop9h 28m

$439

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 9/5

10:17 am-8:56 pm

3 stops31h 39m

San Juan Luis Munoz Marin Intl

Tue 9/9

3:19 pm-7:23 pm

3 stops31h 04m

$448

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 9/8

12:07 pm-8:56 pm

3 stops29h 49m

San Juan Luis Munoz Marin Intl

Sat 9/13

3:19 pm-5:24 pm

3 stops29h 05m

$459

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 $437. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Portland averaging around $451.

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 $565 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 $449 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

Best Price Found	$200
Fastest flight time	8h 13m
Direct flights	None
Airports in Caribbean Islands	8 airports

The best one-way flight to Caribbean Islands from Portland in the past 72 hours is $200. The best round-trip flight deal from Portland to Caribbean Islands found on momondo in the last 72 hours is $389.

The fastest flight from Portland to Caribbean Islands takes 8h 13m

There are no direct flights from Portland to Caribbean Islands. Popular non-direct routes for this connection are Portland Airport - San Juan Luis Munoz Marin Intl Airport, Portland Airport - Nassau Intl Airport and Portland Airport - Punta Cana Airport.

There are 8 airports near Caribbean Islands: Nassau Intl (NAS), Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Castries Hewanorra (UVF), Providenciales (PLS), Oranjestad Reina Beatrix (AUA), San Juan Luis Munoz Marin Intl (SJU)

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 July 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 13.86% of all bookings. The subsequent popular models are Boeing 737 MAX 9 at 11.89%, Boeing 737-900 Passenger/BBJ3 (winglets) at 8.88%, and Boeing 737 at 8.60%.

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 2,914 reviews	Search JetBlue flights
Delta	PriceFrom $212	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
Spirit Airlines	PriceFrom $248	Free Cancellation	Rating 6.3 8,048 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $318	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
American Airlines	PriceFrom $328	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $450	Free Cancellation	Rating 8.0 4,246 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.

Start using Trips

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Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Flights to New Yorkfrom $39

Flights to Londonfrom $283

Flights to Bangkokfrom $515

Flights to Tokyofrom $493

Flights to Los Angelesfrom $37

Flights to Parisfrom $255

Flights to Copenhagenfrom $268

Flights to Istanbulfrom $435

Flights to Manilafrom $523

Flights to Miamifrom $58

Flights to Romefrom $178

Flights to Chicagofrom $59

Cheap flights from Portland to Caribbean Islands from $200

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 10/4. 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

Delta flights from Portland to Caribbean Islands

Our best Delta deals on Portland to Caribbean Islands flight tickets

United Airlines flights from Portland to Caribbean Islands

Our best United Airlines 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 $437. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Portland averaging around $451.

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?

United Airlines, Delta, and Spirit 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

Best Price Found

Fastest flight time

Direct flights

Airports in Caribbean Islands

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