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

Spirit Airlines, Delta, and American Airlines are the most popular carriers operating from Oregon 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 Oregon according to our data. American Airlines is the first choice among our users, with 59% 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.

How long is the flight from Oregon to Caribbean?

If you’re flying from a popular airport in Oregon, such as Medford or Portland, and flying into Caribbean, then you can expect flight times to average 16h 50m and 16h 50m, respectively.

When did momondo last update prices for flights from Oregon to Caribbean?

Prices for flights from Oregon to Caribbean refresh daily.

How many operators does momondo search for flights from Oregon to Caribbean?

The number of operators available for flights from Oregon to Caribbean is 7 as of August 2025.

How old do you have to be to fly from Oregon to Caribbean?

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 Oregon to Caribbean.

What documentation or ID do you need to fly to Caribbean?

The travel and health documents you'll need for your trip to Caribbean 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. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$146 Cheap Flights from Oregon to Caribbean in 2025

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Find the cheapest flights from Oregon to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

7:52 pm - 2:17 pmPDX-SJU

15h 25m2 stops

11:59 am - 7:23 pmSJU-PDX

34h 24m3 stops

$367Spirit Airlines

Find Deal

sáb, ago 30 - qui, set 11

8:58 pm - 6:34 pmBOI-SJU

19h 36m2 stops

7:40 pm - 1:21 pmSJU-BOI

19h 41m2 stops

$370Spirit Airlines

Find Deal

seg, out 27 - sex, out 31

5:15 am - 6:35 pmBOI-SJU

10h 20m2 stops

6:40 am - 4:10 pmSJU-BOI

12h 30m2 stops

$375Southwest

Find Deal

ter, nov 18 - sex, nov 21

5:40 am - 11:58 pmBOI-SJU

15h 18m2 stops

7:00 am - 6:25 pmSJU-BOI

14h 25m2 stops

$385Delta

Find Deal

qua, jan 21 - ter, jan 27

7:10 pm - 10:25 amPDX-SJU

11h 15m2 stops

8:55 am - 7:20 pmSJU-PDX

14h 25m2 stops

$389Southwest

Find Deal

seg, nov 10 - ter, dez 9

10:32 pm - 12:00 pmPDX-SJU

10h 28m1 stop

1:05 am - 12:42 pmSJU-PDX

14h 37m2 stops

$399United Airlines

Find Deal

sáb, out 11 - ter, out 21

3:18 pm - 12:18 pmPDX-SJU

18h 00m2 stops

7:00 am - 11:52 pmSJU-PDX

19h 52m2 stops

$409Delta

Find Deal

seg, set 8 - qua, set 17

1:57 pm - 11:11 amBOI-SJU

19h 14m2 stops

7:05 pm - 12:27 pmSJU-BOI

19h 22m2 stops

$415American Airlines

Find Deal

sáb, set 6 - sáb, set 13

11:59 pm - 5:10 pmPDX-SJU

13h 11m2 stops

5:50 am - 11:16 pmSJU-PDX

21h 26m1 stop

$419American Airlines

Find Deal

ter, dez 2 - qui, dez 11

7:35 pm - 1:45 pmPDX-SJU

15h 10m2 stops

1:05 am - 8:53 amSJU-PDX

10h 48m1 stop

$428United Airlines

Find Deal

dom, set 14 - sáb, set 20

United Airlines flights from Oregon to Caribbean

Our best United Airlines deals on Oregon to Caribbean flight tickets

United Airlines

Oct 11

PDX10:32 pmPortland

10h 28m

1 stop

SJU12:00 pmSan Juan Luis Munoz Marin Intl

Oct 21

SJU1:05 amSan Juan Luis Munoz Marin Intl

14h 37m

2 stops

PDX12:42 pmPortland

$399

Find similar

United Airlines

Sep 14

PDX7:35 pmPortland

15h 10m

2 stops

SJU1:45 pmSan Juan Luis Munoz Marin Intl

Sep 20

SJU1:05 amSan Juan Luis Munoz Marin Intl

10h 48m

1 stop

PDX8:53 amPortland

$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

Southwest flights from Oregon to Caribbean

Our best Southwest deals on Oregon to Caribbean flight tickets

Southwest

Nov 18

BOI5:15 amBoise Air Term. Gowen Fld

10h 20m

2 stops

SJU6:35 pmSan Juan Luis Munoz Marin Intl

Nov 21

SJU6:40 amSan Juan Luis Munoz Marin Intl

12h 30m

2 stops

BOI4:10 pmBoise Air Term. Gowen Fld

$375

Find similar

Southwest

Nov 10

PDX7:10 pmPortland

11h 15m

2 stops

SJU10:25 amSan Juan Luis Munoz Marin Intl

Dec 9

SJU8:55 amSan Juan Luis Munoz Marin Intl

14h 25m

2 stops

PDX7:20 pmPortland

$389

Find similar

Southwest

Nov 10

EUG2:55 pmEugene

18h 20m

2 stops

SJU1:15 pmSan Juan Luis Munoz Marin Intl

Dec 9

SJU8:55 amSan Juan Luis Munoz Marin Intl

16h 20m

2 stops

EUG9:15 pmEugene

$411

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

sáb 8/30

7:52 pm-2:17 pm

2 stops15h 25m

San Juan Luis Munoz Marin Intl

qui 9/11

11:59 am-7:23 pm

3 stops34h 24m

$367

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

seg 10/27

8:58 pm-6:34 pm

2 stops19h 36m

San Juan Luis Munoz Marin Intl

sex 10/31

7:40 pm-1:21 pm

2 stops19h 41m

$370

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

ter 11/18

5:15 am-6:35 pm

2 stops10h 20m

San Juan Luis Munoz Marin Intl

sex 11/21

6:40 am-4:10 pm

2 stops12h 30m

$375

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

qua 1/21

5:40 am-11:58 pm

2 stops15h 18m

San Juan Luis Munoz Marin Intl

ter 1/27

7:00 am-6:25 pm

2 stops14h 25m

$385

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

seg 11/10

7:10 pm-10:25 am

2 stops11h 15m

San Juan Luis Munoz Marin Intl

ter 12/9

8:55 am-7:20 pm

2 stops14h 25m

$389

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

sáb 10/11

10:32 pm-12:00 pm

1 stop10h 28m

San Juan Luis Munoz Marin Intl

ter 10/21

1:05 am-12:42 pm

2 stops14h 37m

$399

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

seg 9/8

3:18 pm-12:18 pm

2 stops18h 00m

San Juan Luis Munoz Marin Intl

qua 9/17

7:00 am-11:52 pm

2 stops19h 52m

$409

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

sáb 9/6

1:57 pm-11:11 am

2 stops19h 14m

San Juan Luis Munoz Marin Intl

sáb 9/13

7:05 pm-12:27 pm

2 stops19h 22m

$415

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

ter 12/2

11:59 pm-5:10 pm

2 stops13h 11m

San Juan Luis Munoz Marin Intl

qui 12/11

5:50 am-11:16 pm

1 stop21h 26m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

dom 9/14

7:35 pm-1:45 pm

2 stops15h 10m

San Juan Luis Munoz Marin Intl

sáb 9/20

1:05 am-8:53 am

1 stop10h 48m

$428

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 Oregon 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

Other information

What is the cheapest month to fly to Caribbean?

In general, October is the cheapest month to fly from Oregon to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $437. If you don’t want to visit Caribbean in October, then you should wait until September to fly from Oregon, when ticket prices are also cheap, with an average price of $451.

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

The cheapest day to depart from Oregon 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 Oregon 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 Oregon when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean 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 from Oregon for as low as $449 on momondo.

Can stopping save me money on Oregon to Caribbean flights?

You could potentially save up to 2% on your flight if you consider stops on a Oregon to Caribbean flight.

Cheap Oregon to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oregon to Caribbean

Best Price Found	$146
Fastest flight time	8h 13m
Direct flights	None
Airports in Caribbean	7 airports

The best one-way flight to Caribbean from Oregon in the past 72 hours is $146. The best round-trip flight deal from Oregon to Caribbean found on momondo in the last 72 hours is $367.

The fastest flight from Oregon to Caribbean takes 8h 13m

There are no direct flights from Oregon to Caribbean. Popular non-direct routes for this connection are Portland Airport - San Juan Luis Munoz Marin Intl Airport, Boise Air Term. Gowen Fld Airport - San Juan Luis Munoz Marin Intl Airport and Portland Airport - Punta Cana Airport.

There are 7 airports near Caribbean: Nassau Intl (NAS), Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Castries Hewanorra (UVF), Oranjestad Reina Beatrix (AUA), San Juan Luis Munoz Marin Intl (SJU)

Search flight deals

When did momondo last update prices for flights from Oregon to Caribbean?
Prices for flights from Oregon to Caribbean refresh daily.
How many operators does momondo search for flights from Oregon to Caribbean?
The number of operators available for flights from Oregon to Caribbean is 7 as of August 2025.
How old do you have to be to fly from Oregon to Caribbean?
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 Oregon to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents you'll need for your trip to Caribbean 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. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Oregon to Caribbean

Compare and see reviews for airlines that fly from Oregon to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
JetBlue	PriceFrom $185	Free Cancellation	Rating 7.2 2,914 reviews	Search JetBlue flights
Delta	PriceFrom $202	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
Spirit Airlines	PriceFrom $248	Free Cancellation	Rating 6.3 8,049 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 Oregon to Caribbean?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean from Oregon.

Can I find flights from Oregon to Caribbean with flexible booking policies on momondo?

All flight searches from Oregon to Caribbean on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Oregon to Caribbean?

momondo provides multiple filters to help you find the best flight to Caribbean from Oregon. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Oregon to Caribbean right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Oregon 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.