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

Frontier, Southwest, and Delta are the most popular carriers operating from Portland to Caribbean

What airlines fly to Caribbean?

American Airlines, Delta and United Airlines 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 60% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 7 different airlines that fly to Caribbean 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?

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 7 operators available for flights from Portland Airport to Caribbean as of November 2025.

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.

$129 Cheap Flights from Portland to Caribbean in 2025/26

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Find the cheapest flights from Portland to Caribbean

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

12:51 pm - 11:56 pmPDX-SJU

31h 05m2 stops

5:14 pm - 5:14 pmSJU-PDX

28h 00m1 stop

$393Multiple Airlines

Find Deal

Thu, Dec 11 - Thu, Dec 18

6:20 am - 11:10 pmPDX-SJU

12h 50m2 stops

5:40 am - 3:40 pmSJU-PDX

14h 00m2 stops

$397Southwest

Find Deal

Sun, Jan 18 - Fri, Jan 23

7:00 am - 11:44 pmPDX-SJU

12h 44m1 stop

7:00 am - 8:32 pmSJU-PDX

17h 32m2 stops

$419Delta

Find Deal

Fri, Jan 23 - Wed, Jan 28

11:05 pm - 12:55 pmPDX-SJU

9h 50m1 stop

2:05 am - 1:45 pmSJU-PDX

15h 40m2 stops

$447United Airlines

Find Deal

Fri, Jan 23 - Tue, Jan 27

8:30 am - 12:36 amPDX-SJU

12h 06m2 stops

7:10 am - 5:46 pmSJU-PDX

13h 36m2 stops

$452United Airlines

Find Deal

Thu, Feb 26 - Tue, Mar 17

7:05 am - 12:59 amPDX-STI

13h 54m1 stop

6:35 am - 8:40 pmSTI-PDX

18h 05m1 stop

$468Delta

Find Deal

Mon, Nov 24 - Tue, Dec 9

10:45 pm - 4:06 pmPDX-SJU

13h 21m1 stop

12:49 pm - 11:23 pmSJU-PDX

14h 34m2 stops

$473American Airlines

Find Deal

Mon, Dec 1 - Tue, Dec 9

10:45 pm - 8:33 pmPDX-STI

17h 48m1 stop

6:00 am - 11:52 pmSTI-PDX

21h 52m1 stop

$481American Airlines

Find Deal

Fri, Dec 5 - Sat, Dec 13

7:00 pm - 12:55 pmPDX-NAS

14h 55m2 stops

9:10 pm - 2:40 pmNAS-PDX

20h 30m2 stops

$535Air Canada

Find Deal

Wed, Dec 3 - Wed, Dec 10

7:00 pm - 12:55 pmPDX-NAS

14h 55m2 stops

9:10 pm - 2:40 pmNAS-PDX

20h 30m2 stops

$536Air Canada

Find Deal

Thu, Nov 27 - Mon, Dec 1

Southwest flights from Portland to Caribbean

Our best Southwest deals on Portland to Caribbean flight tickets

Southwest

Jan 18

PDX6:20 amPortland

12h 50m

2 stops

SJU11:10 pmSan Juan Luis Munoz Marin Intl

Jan 23

SJU5:40 amSan Juan Luis Munoz Marin Intl

14h 00m

2 stops

PDX3:40 pmPortland

$397

Find similar

Southwest

Dec 2

PDX6:15 amPortland

11h 50m

2 stops

SJU10:05 pmSan Juan Luis Munoz Marin Intl

Dec 17

SJU11:20 amSan Juan Luis Munoz Marin Intl

15h 10m

2 stops

PDX10:30 pmPortland

$435

Find similar

Southwest

Dec 1

PDX10:05 amPortland

11h 35m

2 stops

SJU1:40 amSan Juan Luis Munoz Marin Intl

Dec 9

SJU2:05 pmSan Juan Luis Munoz Marin Intl

12h 30m

2 stops

PDX10:35 pmPortland

$444

Find similar

United Airlines flights from Portland to Caribbean

Our best United Airlines deals on Portland to Caribbean flight tickets

United Airlines

Jan 23

PDX11:05 pmPortland

9h 50m

1 stop

SJU12:55 pmSan Juan Luis Munoz Marin Intl

Jan 27

SJU2:05 amSan Juan Luis Munoz Marin Intl

15h 40m

2 stops

PDX1:45 pmPortland

$447

Find similar

United Airlines

Feb 26

PDX8:30 amPortland

12h 06m

2 stops

SJU12:36 amSan Juan Luis Munoz Marin Intl

Mar 17

SJU7:10 amSan Juan Luis Munoz Marin Intl

13h 36m

2 stops

PDX5:46 pmPortland

$452

Find similar

United Airlines

Jan 14

PDX7:00 amPortland

10h 00m

1 stop

SJU9:00 pmSan Juan Luis Munoz Marin Intl

Jan 20

SJU8:10 amSan Juan Luis Munoz Marin Intl

14h 46m

2 stops

PDX6:56 pmPortland

$457

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 12/11

12:51 pm-11:56 pm

2 stops31h 05m

San Juan Luis Munoz Marin Intl

Thu 12/18

5:14 pm-5:14 pm

1 stop28h 00m

$393

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 1/18

6:20 am-11:10 pm

2 stops12h 50m

San Juan Luis Munoz Marin Intl

Fri 1/23

5:40 am-3:40 pm

2 stops14h 00m

$397

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 1/23

7:00 am-11:44 pm

1 stop12h 44m

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

Fri 1/23

11:05 pm-12:55 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-1:45 pm

2 stops15h 40m

$447

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 2/26

8:30 am-12:36 am

2 stops12h 06m

San Juan Luis Munoz Marin Intl

Tue 3/17

7:10 am-5:46 pm

2 stops13h 36m

$452

PortlandSantiago de los Caballeros

PDX - STI

PDXSTI

Portland

Mon 11/24

7:05 am-12:59 am

1 stop13h 54m

Santiago de los Caballeros

Tue 12/9

6:35 am-8:40 pm

1 stop18h 05m

$468

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 12/1

10:45 pm-4:06 pm

1 stop13h 21m

San Juan Luis Munoz Marin Intl

Tue 12/9

12:49 pm-11:23 pm

2 stops14h 34m

$473

PortlandSantiago de los Caballeros

PDX - STI

PDXSTI

Portland

Fri 12/5

10:45 pm-8:33 pm

1 stop17h 48m

Santiago de los Caballeros

Sat 12/13

6:00 am-11:52 pm

1 stop21h 52m

$481

PortlandNassau

PDX - NAS

PDXNAS

Portland

Wed 12/3

7:00 pm-12:55 pm

2 stops14h 55m

Nassau Intl

Wed 12/10

9:10 pm-2:40 pm

2 stops20h 30m

$535

PortlandNassau

PDX - NAS

PDXNAS

Portland

Thu 11/27

7:00 pm-12:55 pm

2 stops14h 55m

Nassau Intl

Mon 12/1

9:10 pm-2:40 pm

2 stops20h 30m

$536

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, October 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 $476. If you don’t want to visit Caribbean in October, then you should wait until September to fly from Portland, when ticket prices are also cheap, with an average price of $481.

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

The cheapest day to depart from Portland to Caribbean is on a Tuesday when prices can be found 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.

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

In the afternoon is the cheapest time of day to fly from Portland to Caribbean when you can find flight prices for as low as $428. Flying to Caribbean in the afternoon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $602.

How far in advance should I book a flight 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 $577 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 $472 on momondo.

Can stopping save me money on Portland to Caribbean flights?

You could potentially save up to 14% 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

Direct flights	None

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

Search flight deals

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 7 operators available for flights from Portland Airport to Caribbean as of November 2025.
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
JetBlue	PriceFrom $185	Free Cancellation	Rating 7.2 2,907 reviews	Search JetBlue flights
Delta	PriceFrom $190	Free Cancellation	Rating 7.9 8,004 reviews	Search Delta flights
Spirit Airlines	PriceFrom $248	Free Cancellation	Rating 6.3 8,115 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $343	Free Cancellation	Rating 7.2 11,042 reviews	Search American Airlines flights
United Airlines	PriceFrom $400	Free Cancellation	Rating 7.4 9,004 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $431	Free Cancellation	Rating 8.0 11,242 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $444	Free Cancellation	Rating 8.0 4,240 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.