Find Deals on Flights from Portland to Caribbean

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Portland to Caribbean

(Round-trip)
Depart: Mon Feb 13 2017 Return: Wed Feb 15 2017 Trip spans 3 days
American Airlines
American Airlines
PWM
SJU
10h 00m
2 stops
SJU
PWM
11h 40m
2 stops
Depart: Mon Feb 6 2017 Return: Mon Feb 13 2017 Trip spans 8 days
United
United
PWM
SJU
6h 30m
1 stop
SJU
PWM
8h 40m
1 stop
Depart: Mon Mar 6 2017 Return: Wed Mar 8 2017 Trip spans 3 days
Major Airline
Major Airline
PWM
SJU
12h 38m
2 stops
SJU
PWM
9h 26m
2 stops
Depart: Mon Feb 6 2017 Return: Sat Feb 11 2017 Trip spans 6 days
JetBlue
JetBlue
PWM
BGI
20h 14m
2 stops
BGI
PWM
9h 29m
1 stop
Depart: Tue Mar 21 2017 Return: Tue Mar 28 2017 Trip spans 8 days
Delta
Delta
PWM
NAS
17h 49m
2 stops
NAS
PWM
15h 15m
2 stops
Depart: Wed Apr 26 2017 Return: Tue May 2 2017 Trip spans 7 days
American Airlines
American Airlines
PWM
SJU
9h 24m
2 stops
SJU
PWM
10h 38m
2 stops
Depart: Sun Feb 12 2017 Return: Fri Feb 17 2017 Trip spans 6 days
United
United
PWM
BQN
7h 05m
1 stop
BQN
PWM
8h 08m
1 stop
Depart: Sat Apr 29 2017 Return: Wed May 10 2017 Trip spans 12 days
American Airlines
American Airlines
PWM
SJU
6h 09m
1 stop
SJU
PWM
10h 31m
2 stops
Depart: Fri Jun 9 2017 Return: Tue Jun 20 2017 Trip spans 12 days
JetBlue
JetBlue
PWM
SJU
6h 34m
1 stop
SJU
PWM
8h 03m
1 stop
Depart: Mon Feb 6 2017 Return: Fri Feb 10 2017 Trip spans 5 days
Major Airline
Major Airline
PWM
PUJ
19h 39m
1 stop
PUJ
PWM
15h 48m
1 stop
Depart: Thu Apr 6 2017 Return: Mon Apr 10 2017 Trip spans 5 days
Delta
Delta
PWM
NAS
29h 13m
2 stops
NAS
PWM
27h 32m
2 stops
Depart: Tue Jan 31 2017 Return: Tue Feb 14 2017 Trip spans 15 days
American Airlines
American Airlines
PWM
SJU
11h 30m
2 stops
SJU
PWM
10h 55m
2 stops
Depart: Wed Feb 8 2017 Return: Wed Feb 15 2017 Trip spans 8 days
JetBlue
JetBlue
PWM
STT
16h 01m
2 stops
STT
PWM
18h 26m
2 stops
Depart: Mon Mar 13 2017 Return: Tue Mar 14 2017 Trip spans 2 days
United
United
PWM
NAS
21h 17m
2 stops
NAS
PWM
17h 58m
2 stops
Depart: Wed Mar 22 2017 Return: Tue Mar 28 2017 Trip spans 7 days
Major Airline
Major Airline
PWM
AUA
8h 49m
2 stops
AUA
PWM
19h 56m
2 stops
Depart: Mon Feb 6 2017 Return: Fri Feb 10 2017 Trip spans 5 days
Delta
Delta
PWM
NAS
18h 11m
2 stops
NAS
PWM
15h 01m
2 stops
Depart: Tue Mar 7 2017 Return: Tue Mar 14 2017 Trip spans 7 days
United
United
PWM
SDQ
26h 03m
1 stop
SDQ
PWM
8h 40m
1 stop
Depart: Sat May 13 2017 Return: Fri May 19 2017 Trip spans 7 days
American Airlines
American Airlines
PWM
SJU
9h 09m
2 stops
SJU
PWM
8h 48m
1 stop
Depart: Wed Mar 8 2017 Return: Mon Mar 13 2017 Trip spans 5 days
Delta
Delta
PWM
PLS
7h 40m
1 stop
PLS
PWM
9h 24m
1 stop
Depart: Fri Feb 10 2017 Return: Wed Feb 15 2017 Trip spans 6 days
Major Airline
Major Airline
PWM
AUA
23h 05m
2 stops
AUA
PWM
21h 04m
2 stops
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Portland
$296
Destination

Aguadilla
$299
Bridgetown
$341
Santo Domingo
$362
Nassau
$357
Providenciales
$393
San Juan
$296
Saint Thomas Island
$354
Oranjestad
$390
Punta Cana
$374