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 52% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 5 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, Delta, and American 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 5 operators available for flights from Portland Airport to Caribbean as of October 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.

$170 Cheap Flights from Portland to Caribbean in 2026/27

Discover deals from 900+ travel sites with momondo.

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.

10:00 pm - 2:19 pmPDX Portland-STT Saint Thomas Island Cyril E King

12h 19m1 stop Miami

6:24 pm - 12:39 pmSTT Saint Thomas Island Cyril E King-PDX Portland

22h 15m2 stops Miami Chicago O'Hare Intl

$480American Airlines

Sun, Feb 21 - Fri, Feb 26

2:48 pm - 12:24 pmPDX Portland-STT Saint Thomas Island Cyril E King

17h 36m2 stops Phoenix Sky Harbor Intl Miami

3:00 pm - 11:11 amSTT Saint Thomas Island Cyril E King-PDX Portland

24h 11m2 stops Miami Dallas/Fort Worth

$480American Airlines

Mon, Jan 11 - Fri, Jan 15

7:15 pm - 8:40 pmPDX Portland-PUJ Punta Cana

22h 25m2 stops Vancouver Intl Toronto Pearson Intl

7:45 pm - 6:31 pmPUJ Punta Cana-PDX Portland

26h 46m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl

$493Air Canada

Fri, Oct 30 - Sat, Nov 7

9:45 pm - 12:55 pmPDX Portland-MBJ Montego Bay Sangster Intl

12h 10m1 stop Atlanta Hartsfield-Jackson

2:20 pm - 10:26 pmMBJ Montego Bay Sangster Intl-PDX Portland

11h 06m1 stop Atlanta Hartsfield-Jackson

$494Delta

Sun, Jan 17 - Thu, Jan 21

11:55 am - 11:10 amPDX Portland-MBJ Montego Bay Sangster Intl

20h 15m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

4:50 pm - 8:41 amMBJ Montego Bay Sangster Intl-PDX Portland

18h 51m2 stops Atlanta Hartsfield-Jackson Seattle/Tacoma Intl

$498Delta

Tue, Jan 5 - Thu, Jan 14

7:00 am - 2:49 amPDX Portland-SJU San Juan Luis Munoz Marin Intl

15h 49m1 stop Miami

3:54 am - 8:32 pmSJU San Juan Luis Munoz Marin Intl-PDX Portland

20h 38m1 stop Miami

$516Multiple Airlines

Wed, Jan 6 - Tue, Jan 12

3:40 pm - 12:13 pmPDX Portland-MBJ Montego Bay Sangster Intl

17h 33m2 stops San Francisco Newark

2:54 pm - 9:40 amMBJ Montego Bay Sangster Intl-PDX Portland

21h 46m2 stops Chicago O'Hare Intl Denver Intl

$518United Airlines

Mon, Feb 1 - Sun, Feb 7

7:15 pm - 11:05 amPDX Portland-STT Saint Thomas Island Cyril E King

12h 50m2 stops Denver Intl Newark

1:07 pm - 12:54 amSTT Saint Thomas Island Cyril E King-PDX Portland

15h 47m2 stops Washington, D.C. Dulles Intl San Francisco

$518United Airlines

Wed, Oct 28 - Sun, Nov 1

6:50 am - 11:05 pmPDX Portland-SJU San Juan Luis Munoz Marin Intl

12h 15m2 stops Chicago Midway Baltimore/Washington

7:35 am - 7:00 pmSJU San Juan Luis Munoz Marin Intl-PDX Portland

15h 25m2 stops Tampa Denver Intl

$546Southwest

Fri, Jan 29 - Mon, Feb 8

5:55 am - 9:20 pmPDX Portland-SJU San Juan Luis Munoz Marin Intl

11h 25m2 stops Phoenix Sky Harbor Intl Tampa

3:15 pm - 1:00 amSJU San Juan Luis Munoz Marin Intl-PDX Portland

13h 45m2 stops Orlando Phoenix Sky Harbor Intl

$546Southwest

Sat, Nov 14 - Sat, Nov 21

Cheap last minute flights

Enter your travel dates to find the best prices.

7:45 pm - 12:45 pmPDX Portland-PUJ Punta Cana

38h 00m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl

12:05 pm - 10:26 amPUJ Punta Cana-PDX Portland

25h 21m2 stops Toronto Pearson Intl Vancouver Intl

$557Air Canada

Fri, Oct 23 - Sat, Oct 31

7:45 pm - 5:45 pmPDX Portland-PUJ Punta Cana

43h 00m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl

10:40 pm - 9:46 pmPUJ Punta Cana-PDX Portland

26h 06m2 stops Toronto Pearson Intl Vancouver Intl

$557Air Canada

Fri, Oct 23 - Sat, Oct 31

5:00 am - 3:45 pmPDX Portland-MBJ Montego Bay Sangster Intl

8h 45m1 stop Denver Intl

3:45 pm - 11:15 pmMBJ Montego Bay Sangster Intl-PDX Portland

10h 30m1 stop Houston George Bush Intcntl

$618United Airlines

Sat, Oct 24 - Sun, Nov 1

7:33 pm - 1:14 pmPDX Portland-MBJ Montego Bay Sangster Intl

15h 41m2 stops San Francisco Newark

3:45 pm - 11:15 pmMBJ Montego Bay Sangster Intl-PDX Portland

10h 30m1 stop Houston George Bush Intcntl

$618United Airlines

Sat, Oct 24 - Sun, Nov 1

3:00 pm - 11:18 amPDX Portland-MBJ Montego Bay Sangster Intl

18h 18m2 stops Phoenix Sky Harbor Intl Miami

6:09 pm - 11:07 amMBJ Montego Bay Sangster Intl-PDX Portland

19h 58m2 stops Miami Dallas/Fort Worth

$637American Airlines

Sat, Oct 24 - Sun, Nov 1

11:00 pm - 3:27 pmPDX Portland-MBJ Montego Bay Sangster Intl

14h 27m1 stop Atlanta Hartsfield-Jackson

5:44 pm - 10:42 amMBJ Montego Bay Sangster Intl-PDX Portland

19h 58m1 stop Atlanta Hartsfield-Jackson

$638Delta

Sat, Oct 24 - Thu, Nov 5

11:00 pm - 11:51 amPDX Portland-MBJ Montego Bay Sangster Intl

10h 51m1 stop Atlanta Hartsfield-Jackson

2:16 pm - 9:49 pmMBJ Montego Bay Sangster Intl-PDX Portland

10h 33m1 stop Atlanta Hartsfield-Jackson

$638Delta

Sat, Oct 24 - Fri, Nov 6

6:40 am - 11:50 pmPDX Portland-SJU San Juan Luis Munoz Marin Intl

14h 10m2 stops Sacramento Intl Orlando

12:40 pm - 10:20 pmSJU San Juan Luis Munoz Marin Intl-PDX Portland

12h 40m2 stops Orlando Las Vegas Harry Reid Intl

$702Southwest

Wed, Oct 21 - Wed, Oct 28

6:30 am - 10:09 pmPDX Portland-SJU San Juan Luis Munoz Marin Intl

12h 39m2 stops Dallas/Fort Worth Miami

7:30 am - 5:48 pmSJU San Juan Luis Munoz Marin Intl-PDX Portland

14h 18m2 stops Miami Dallas/Fort Worth

$707American Airlines

Wed, Oct 21 - Tue, Nov 3

7:35 pm - 9:20 amPDX Portland-SJU San Juan Luis Munoz Marin Intl

10h 45m2 stops Denver Intl Orlando

10:45 am - 9:30 pmSJU San Juan Luis Munoz Marin Intl-PDX Portland

14h 45m2 stops Orlando Phoenix Sky Harbor Intl

$722Southwest

Thu, Oct 22 - Tue, Nov 3

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Delta flights from Portland to Caribbean

Our best Delta deals on Portland to Caribbean flight tickets

Delta

Jan 17

PDX9:45 pmPortland

12h 10m

1 stop

MBJ12:55 pmMontego Bay Sangster Intl

Jan 21

MBJ2:20 pmMontego Bay Sangster Intl

11h 06m

1 stop

PDX10:26 pmPortland

$494

Delta

Jan 17

PDX5:45 pmPortland

14h 25m

2 stops

MBJ11:10 amMontego Bay Sangster Intl

Jan 22

MBJ4:50 pmMontego Bay Sangster Intl

23h 18m

2 stops

PDX1:08 pmPortland

$498

Delta

Jan 11

PDX7:40 pmPortland

13h 40m

2 stops

STT1:20 pmSaint Thomas Island Cyril E King

Jan 15

STT1:50 pmSaint Thomas Island Cyril E King

12h 36m

1 stop

PDX10:26 pmPortland

$500

United Airlines flights from Portland to Caribbean

Our best United Airlines deals on Portland to Caribbean flight tickets

United Airlines

Oct 28

PDX7:15 pmPortland

12h 50m

2 stops

STT11:05 amSaint Thomas Island Cyril E King

Nov 1

STT1:07 pmSaint Thomas Island Cyril E King

11h 08m

1 stop

PDX8:15 pmPortland

$518

United Airlines

Oct 30

PDX7:15 pmPortland

12h 50m

2 stops

STT11:05 amSaint Thomas Island Cyril E King

Nov 3

STT1:07 pmSaint Thomas Island Cyril E King

11h 08m

1 stop

PDX8:15 pmPortland

$538

United Airlines

Feb 21

PDX10:56 pmPortland

12h 18m

1 stop

MBJ2:14 pmMontego Bay Sangster Intl

Mar 2

MBJ1:25 pmMontego Bay Sangster Intl

23h 15m

2 stops

PDX9:40 amPortland

$544

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSaint Thomas Island

PDX Portland - STT Saint Thomas Island Cyril E King

PDXSTT

Portland

Sun 2/21

10:00 pm-2:19 pm

1 stop12h 19m

Saint Thomas Island Cyril E King

Fri 2/26

6:24 pm-12:39 pm

2 stops22h 15m

$480

PortlandSaint Thomas Island

PDX Portland - STT Saint Thomas Island Cyril E King

PDXSTT

Portland

Mon 1/11

2:48 pm-12:24 pm

2 stops17h 36m

Saint Thomas Island Cyril E King

Fri 1/15

3:00 pm-11:11 am

2 stops24h 11m

$480

PortlandPunta Cana

PDX Portland - PUJ Punta Cana

PDXPUJ

Portland

Fri 10/30

7:15 pm-8:40 pm

2 stops22h 25m

Punta Cana

Sat 11/7

7:45 pm-6:31 pm

2 stops26h 46m

$493

Quickest round-trip

PortlandMontego Bay

PDX Portland - MBJ Montego Bay Sangster Intl

PDXMBJ

Portland

Sun 1/17

9:45 pm-12:55 pm

1 stop12h 10m

Montego Bay Sangster Intl

Thu 1/21

2:20 pm-10:26 pm

1 stop11h 06m

$494

PortlandMontego Bay

PDX Portland - MBJ Montego Bay Sangster Intl

PDXMBJ

Portland

Tue 1/5

11:55 am-11:10 am

2 stops20h 15m

Montego Bay Sangster Intl

Thu 1/14

4:50 pm-8:41 am

2 stops18h 51m

$498

PortlandSan Juan

PDX Portland - SJU San Juan Luis Munoz Marin Intl

PDXSJU

Portland

Wed 1/6

7:00 am-2:49 am

1 stop15h 49m

San Juan Luis Munoz Marin Intl

Tue 1/12

3:54 am-8:32 pm

1 stop20h 38m

$516

PortlandMontego Bay

PDX Portland - MBJ Montego Bay Sangster Intl

PDXMBJ

Portland

Mon 2/1

3:40 pm-12:13 pm

2 stops17h 33m

Montego Bay Sangster Intl

Sun 2/7

2:54 pm-9:40 am

2 stops21h 46m

$518

PortlandSaint Thomas Island

PDX Portland - STT Saint Thomas Island Cyril E King

PDXSTT

Portland

Wed 10/28

7:15 pm-11:05 am

2 stops12h 50m

Saint Thomas Island Cyril E King

Sun 11/1

1:07 pm-12:54 am

2 stops15h 47m

$518

PortlandSan Juan

PDX Portland - SJU San Juan Luis Munoz Marin Intl

PDXSJU

Portland

Fri 1/29

6:50 am-11:05 pm

2 stops12h 15m

San Juan Luis Munoz Marin Intl

Mon 2/8

7:35 am-7:00 pm

2 stops15h 25m

$546

PortlandSan Juan

PDX Portland - SJU San Juan Luis Munoz Marin Intl

PDXSJU

Portland

Sat 11/14

5:55 am-9:20 pm

2 stops11h 25m

San Juan Luis Munoz Marin Intl

Sat 11/21

3:15 pm-1:00 am

2 stops13h 45m

$546

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, January 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 $639. If you don’t want to visit Caribbean in January, then you should wait until August to fly from Portland, when ticket prices are also cheap, with an average price of $653.

How far in advance should I book a flight from Portland 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 $593 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 27% 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

Best Price Found	$170
Fastest flight time	8h 14m
Direct flights	None

The best one-way flight to Caribbean from Portland in the past 72 hours is $170. The best round-trip flight deal from Portland to Caribbean found on momondo in the last 72 hours is $480.

The fastest flight from Portland to Caribbean takes 8h 14m

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

Search flight deals

Frequently asked questions about flying 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 5 operators available for flights from Portland Airport to Caribbean as of October 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 $235	Free Cancellation	Rating 7.8 8,654 reviews	Search Delta flights
United Airlines	PriceFrom $247	Free Cancellation	Rating 7.4 10,382 reviews	Search United Airlines flights
JetBlue	PriceFrom $261	Free Cancellation	Rating 7.1 3,056 reviews	Search JetBlue flights
American Airlines	PriceFrom $392	Free Cancellation	Rating 7.0 12,177 reviews	Search American Airlines flights
Southwest	PriceFrom $408	Free Cancellation	Rating 7.9 4,214 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.