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 61% 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.

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

Spirit Airlines, Delta, and United Airlines 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 7 operators available for flights from Portland Airport to Caribbean as of August 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.

$162 Cheap Flights from Portland to Caribbean in 2025

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Find the cheapest flights from Portland to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

12:52 pm - 1:19 pmPDX-SJU

21h 27m2 stops

2:11 am - 11:56 amSJU-PDX

13h 45m2 stops

$359Frontier

Find Deal

Thu, Oct 30 - Fri, Nov 7

8:36 pm - 12:36 amPDX-SJU

25h 00m2 stops

11:51 am - 11:42 amSJU-PDX

26h 51m3 stops

$383Spirit Airlines

Find Deal

Wed, Oct 22 - Thu, Oct 30

7:45 pm - 1:07 pmPDX-SJU

13h 22m2 stops

2:10 pm - 10:39 pmSJU-PDX

12h 29m1 stop

$399Delta

Find Deal

Wed, Jan 21 - Wed, Jan 28

7:00 am - 8:26 pmPDX-SJU

10h 26m1 stop

1:05 am - 1:47 pmSJU-PDX

15h 42m2 stops

$419United Airlines

Find Deal

Mon, Oct 27 - Fri, Oct 31

10:57 pm - 11:45 amPDX-SJU

8h 48m1 stop

7:20 am - 8:24 pmSJU-PDX

17h 04m1 stop

$424American Airlines

Find Deal

Sun, Feb 15 - Sat, Feb 21

10:17 pm - 12:00 pmPDX-SJU

10h 43m1 stop

1:30 pm - 9:26 pmSJU-PDX

10h 56m1 stop

$430United Airlines

Find Deal

Fri, Oct 10 - Sat, Oct 18

6:55 pm - 10:25 amPDX-SJU

11h 30m2 stops

8:55 am - 7:20 pmSJU-PDX

14h 25m2 stops

$431Southwest

Find Deal

Wed, Dec 3 - Wed, Dec 10

3:15 pm - 11:56 amPDX-PUJ

16h 41m2 stops

5:30 pm - 11:09 amPUJ-PDX

21h 39m2 stops

$436American Airlines

Find Deal

Sat, Nov 8 - Tue, Nov 11

3:19 pm - 12:56 pmPDX-SJU

17h 37m2 stops

7:00 am - 7:19 pmSJU-PDX

16h 19m2 stops

$447Delta

Find Deal

Mon, Nov 3 - Thu, Nov 20

7:10 pm - 10:25 amPDX-SJU

11h 15m2 stops

8:55 am - 6:15 pmSJU-PDX

13h 20m2 stops

$451Southwest

Find Deal

Sun, Nov 2 - Wed, Nov 5

Frontier flights from Portland to Caribbean

Our best Frontier deals on Portland to Caribbean flight tickets

Frontier

Oct 30

PDX12:52 pmPortland

21h 27m

2 stops

SJU1:19 pmSan Juan Luis Munoz Marin Intl

Nov 7

SJU2:11 amSan Juan Luis Munoz Marin Intl

13h 45m

2 stops

PDX11:56 amPortland

$359

Find similar

Frontier

Sep 17

PDX7:15 amPortland

23h 37m

2 stops

SJU9:52 amSan Juan Luis Munoz Marin Intl

Sep 25

SJU8:00 amSan Juan Luis Munoz Marin Intl

19h 12m

2 stops

PDX12:12 amPortland

$398

Find similar

Frontier

Nov 7

PDX3:26 pmPortland

15h 53m

2 stops

SJU11:19 amSan Juan Luis Munoz Marin Intl

Nov 16

SJU2:11 amSan Juan Luis Munoz Marin Intl

13h 45m

2 stops

PDX11:56 amPortland

$472

Find similar

Spirit Airlines flights from Portland to Caribbean

Our best Spirit Airlines deals on Portland to Caribbean flight tickets

Spirit Airlines

Oct 22

PDX8:36 pmPortland

25h 00m

2 stops

SJU12:36 amSan Juan Luis Munoz Marin Intl

Oct 30

SJU11:51 amSan Juan Luis Munoz Marin Intl

26h 51m

3 stops

PDX11:42 amPortland

$383

Find similar

Spirit Airlines

Oct 1

PDX12:07 pmPortland

22h 36m

2 stops

SJU1:43 pmSan Juan Luis Munoz Marin Intl

Oct 27

SJU3:19 pmSan Juan Luis Munoz Marin Intl

31h 17m

3 stops

PDX7:36 pmPortland

$385

Find similar

Spirit Airlines

Oct 1

PDX12:07 pmPortland

22h 36m

2 stops

SJU1:43 pmSan Juan Luis Munoz Marin Intl

Oct 6

SJU7:43 pmSan Juan Luis Munoz Marin Intl

26h 53m

2 stops

PDX7:36 pmPortland

$386

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 10/30

12:52 pm-1:19 pm

2 stops21h 27m

San Juan Luis Munoz Marin Intl

Fri 11/7

2:11 am-11:56 am

2 stops13h 45m

$359

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 10/22

8:36 pm-12:36 am

2 stops25h 00m

San Juan Luis Munoz Marin Intl

Thu 10/30

11:51 am-11:42 am

3 stops26h 51m

$383

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 1/21

7:45 pm-1:07 pm

2 stops13h 22m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:10 pm-10:39 pm

1 stop12h 29m

$399

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 10/27

7:00 am-8:26 pm

1 stop10h 26m

San Juan Luis Munoz Marin Intl

Fri 10/31

1:05 am-1:47 pm

2 stops15h 42m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 2/15

10:57 pm-11:45 am

1 stop8h 48m

San Juan Luis Munoz Marin Intl

Sat 2/21

7:20 am-8:24 pm

1 stop17h 04m

$424

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 10/10

10:17 pm-12:00 pm

1 stop10h 43m

San Juan Luis Munoz Marin Intl

Sat 10/18

1:30 pm-9:26 pm

1 stop10h 56m

$430

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 12/3

6:55 pm-10:25 am

2 stops11h 30m

San Juan Luis Munoz Marin Intl

Wed 12/10

8:55 am-7:20 pm

2 stops14h 25m

$431

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Sat 11/8

3:15 pm-11:56 am

2 stops16h 41m

Punta Cana

Tue 11/11

5:30 pm-11:09 am

2 stops21h 39m

$436

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 11/3

3:19 pm-12:56 pm

2 stops17h 37m

San Juan Luis Munoz Marin Intl

Thu 11/20

7:00 am-7:19 pm

2 stops16h 19m

$447

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 11/2

7:10 pm-10:25 am

2 stops11h 15m

San Juan Luis Munoz Marin Intl

Wed 11/5

8:55 am-6:15 pm

2 stops13h 20m

$451

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, September 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 $453. If you don’t want to visit Caribbean in September, then you should wait until October to fly from Portland, when ticket prices are also cheap, with an average price of $489.

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 $574 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 $438 on momondo.

Can stopping save me money on Portland to Caribbean flights?

You could potentially save up to 6% 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 August 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 2,920 reviews	Search JetBlue flights
Delta	PriceFrom $212	Free Cancellation	Rating 7.9 7,976 reviews	Search Delta flights
Spirit Airlines	PriceFrom $248	Free Cancellation	Rating 6.3 8,013 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $340	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $343	Free Cancellation	Rating 7.4 8,942 reviews	Search United Airlines flights
Southwest	PriceFrom $450	Free Cancellation	Rating 8.0 4,241 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?

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.