What airlines fly to Caribbean?

American Airlines, United Airlines and Delta 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 54% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 6 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?

Frontier, Southwest, and Air Canada 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 6 operators available for flights from Portland Airport to Caribbean as of February 2026.

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.

$138 Cheap Flights from Portland to Caribbean in 2026

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Find the cheapest flights from Portland to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:59 pm - 2:04 pm

PDX

MBJ

12h 05m

1 stop

1:27 pm - 11:44 pm

MBJ

PDX

12h 17m

1 stop

$352American Airlines

Sun, Mar 8 - Wed, Mar 11

11:40 pm - 3:37 pm

PDX

MBJ

13h 57m

2 stops

4:37 pm - 11:01 am

MBJ

PDX

20h 24m

2 stops

$357American Airlines

Sat, May 2 - Thu, May 7

11:59 pm - 12:46 pm

PDX

MBJ

10h 47m

1 stop

1:48 pm - 10:45 pm

MBJ

PDX

10h 57m

1 stop

$362United Airlines

Sun, Mar 8 - Wed, Mar 11

10:54 pm - 1:37 pm

PDX

MBJ

12h 43m

1 stop

2:20 pm - 9:54 am

MBJ

PDX

21h 34m

2 stops

$367United Airlines

Sun, Mar 8 - Wed, Mar 11

11:23 pm - 1:25 pm

PDX

MBJ

12h 02m

1 stop

12:56 pm - 11:53 pm

MBJ

PDX

12h 57m

1 stop

$382American Airlines

Tue, Apr 7 - Thu, Apr 16

3:00 pm - 10:35 am

PDX

SJU

16h 35m

2 stops

11:25 am - 10:00 pm

SJU

PDX

13h 35m

2 stops

$386Southwest

Mon, Apr 27 - Wed, May 6

3:00 pm - 10:35 am

PDX

SJU

16h 35m

2 stops

10:00 am - 10:40 pm

SJU

PDX

15h 40m

2 stops

$405Southwest

Mon, May 4 - Fri, May 8

11:40 pm - 11:00 pm

PDX

SJU

20h 20m

1 stop

1:45 pm - 10:25 pm

SJU

PDX

11h 40m

1 stop

$411JetBlue

Mon, May 25 - Thu, May 28

7:43 pm - 11:21 am

PDX

MBJ

13h 38m

2 stops

11:15 am - 10:23 pm

MBJ

PDX

13h 08m

2 stops

$427Delta

Sun, Mar 8 - Wed, Mar 11

12:30 am - 1:27 pm

PDX

MBJ

10h 57m

1 stop

2:10 pm - 10:02 pm

MBJ

PDX

9h 52m

1 stop

$442Delta

Tue, Apr 7 - Tue, Apr 21

Southwest flights from Portland to Caribbean

Our best Southwest deals on Portland to Caribbean flight tickets

Southwest

Apr 27

PDX3:00 pmPortland

16h 35m

2 stops

SJU10:35 amSan Juan Luis Munoz Marin Intl

May 8

SJU10:00 amSan Juan Luis Munoz Marin Intl

15h 40m

2 stops

PDX10:40 pmPortland

$386

Southwest

May 4

PDX3:00 pmPortland

16h 35m

2 stops

SJU10:35 amSan Juan Luis Munoz Marin Intl

May 8

SJU10:00 amSan Juan Luis Munoz Marin Intl

15h 40m

2 stops

PDX10:40 pmPortland

$405

Southwest

Apr 28

PDX9:45 amPortland

10h 55m

2 stops

SJU11:40 pmSan Juan Luis Munoz Marin Intl

May 5

SJU5:05 amSan Juan Luis Munoz Marin Intl

18h 55m

2 stops

PDX9:00 pmPortland

$406

JetBlue flights from Portland to Caribbean

Our best JetBlue deals on Portland to Caribbean flight tickets

JetBlue

May 25

PDX11:40 pmPortland

20h 20m

1 stop

SJU11:00 pmSan Juan Luis Munoz Marin Intl

May 28

SJU1:45 pmSan Juan Luis Munoz Marin Intl

11h 40m

1 stop

PDX10:25 pmPortland

$411

JetBlue

Jun 1

PDX11:40 pmPortland

20h 20m

1 stop

SJU11:00 pmSan Juan Luis Munoz Marin Intl

Jun 5

SJU1:45 pmSan Juan Luis Munoz Marin Intl

11h 40m

1 stop

PDX10:25 pmPortland

$495

JetBlue

May 22

PDX11:40 pmPortland

20h 20m

1 stop

SJU11:00 pmSan Juan Luis Munoz Marin Intl

May 29

SJU1:45 pmSan Juan Luis Munoz Marin Intl

11h 40m

1 stop

PDX10:25 pmPortland

$496

Fly from

Fly to

Route

Depart

Return

Price

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sun 3/8

11:59 pm-2:04 pm

1 stop12h 05m

Montego Bay Sangster Intl

Wed 3/11

1:27 pm-11:44 pm

1 stop12h 17m

$352

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sat 5/2

11:40 pm-3:37 pm

2 stops13h 57m

Montego Bay Sangster Intl

Thu 5/7

4:37 pm-11:01 am

2 stops20h 24m

$357

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sun 3/8

11:59 pm-12:46 pm

1 stop10h 47m

Montego Bay Sangster Intl

Wed 3/11

1:48 pm-10:45 pm

1 stop10h 57m

$362

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sun 3/8

10:54 pm-1:37 pm

1 stop12h 43m

Montego Bay Sangster Intl

Wed 3/11

2:20 pm-9:54 am

2 stops21h 34m

$367

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Tue 4/7

11:23 pm-1:25 pm

1 stop12h 02m

Montego Bay Sangster Intl

Thu 4/16

12:56 pm-11:53 pm

1 stop12h 57m

$382

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 4/27

3:00 pm-10:35 am

2 stops16h 35m

San Juan Luis Munoz Marin Intl

Wed 5/6

11:25 am-10:00 pm

2 stops13h 35m

$386

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 5/4

3:00 pm-10:35 am

2 stops16h 35m

San Juan Luis Munoz Marin Intl

Fri 5/8

10:00 am-10:40 pm

2 stops15h 40m

$405

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 5/25

11:40 pm-11:00 pm

1 stop20h 20m

San Juan Luis Munoz Marin Intl

Thu 5/28

1:45 pm-10:25 pm

1 stop11h 40m

$411

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sun 3/8

7:43 pm-11:21 am

2 stops13h 38m

Montego Bay Sangster Intl

Wed 3/11

11:15 am-10:23 pm

2 stops13h 08m

$427

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Tue 4/7

12:30 am-1:27 pm

1 stop10h 57m

Montego Bay Sangster Intl

Tue 4/21

2:10 pm-10:02 pm

1 stop9h 52m

$442

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 $468. 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 $498.

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 $581 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 $505 on momondo.

Can stopping save me money on Portland to Caribbean flights?

You could potentially save up to 12% 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

Fastest flight time	8h 55m
Direct flights	None

The fastest flight from Portland to Caribbean takes 8h 55m

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 6 operators available for flights from Portland Airport to Caribbean as of February 2026.
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
Delta	PriceFrom $184	Free Cancellation	Rating 7.9 8,205 reviews	Search Delta flights
JetBlue	PriceFrom $185	Free Cancellation	Rating 7.2 2,897 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $213	Free Cancellation	Rating 6.3 8,464 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $327	Free Cancellation	Rating 7.4 9,308 reviews	Search United Airlines flights
American Airlines	PriceFrom $399	Free Cancellation	Rating 7.2 11,294 reviews	Search American Airlines flights
Southwest	PriceFrom $408	Free Cancellation	Rating 8.0 4,289 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.