Find Cheap 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
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Portland to Caribbean

(Round-trip)
Depart: Sat Oct 14 2017 Return: Mon Oct 16 2017 Trip spans 3 days
Major Airline
Major Airline
PWM
SJU
8h 49m
3 stops
SJU
PWM
12h 59m
3 stops
Depart: Wed Dec 6 2017 Return: Wed Dec 13 2017 Trip spans 8 days
Delta
Delta
PWM
SJU
6h 08m
1 stop
SJU
PWM
7h 45m
1 stop
Depart: Wed Oct 4 2017 Return: Wed Oct 11 2017 Trip spans 8 days
American Airlines
American Airlines
PWM
GCM
19h 15m
1 stop
GCM
PWM
22h 22m
1 stop
Depart: Fri Aug 25 2017 Return: Sat Sep 2 2017 Trip spans 9 days
United
United
PWM
SJU
27h 50m
1 stop
SJU
PWM
20h 43m
2 stops
Depart: Fri Jul 21 2017 Return: Mon Jul 24 2017 Trip spans 4 days
JetBlue
JetBlue
PWM
BGI
7h 04m
1 stop
BGI
PWM
12h 58m
1 stop
Depart: Fri Dec 8 2017 Return: Sat Dec 23 2017 Trip spans 16 days
Major Airline
Major Airline
PWM
PLS
7h 24m
3 stops
PLS
PWM
27h 21m
3 stops
Depart: Wed Nov 1 2017 Return: Wed Nov 15 2017 Trip spans 15 days
Delta
Delta
PWM
SDQ
9h 47m
1 stop
SDQ
PWM
8h 58m
1 stop
Depart: Sun Dec 3 2017 Return: Sun Dec 10 2017 Trip spans 8 days
American Airlines
American Airlines
PWM
PUJ
22h 35m
1 stop
PUJ
PWM
27h 16m
1 stop
Depart: Tue Oct 3 2017 Return: Thu Oct 19 2017 Trip spans 17 days
Delta
Delta
PWM
STI
6h 13m
1 stop
STI
PWM
16h 43m
1 stop
Depart: Tue Jul 11 2017 Return: Mon Jul 17 2017 Trip spans 7 days
United
United
PWM
SJU
15h 40m
1 stop
SJU
PWM
9h 43m
1 stop
Depart: Sun Dec 10 2017 Return: Sat Dec 16 2017 Trip spans 7 days
American Airlines
American Airlines
PWM
PUJ
22h 35m
1 stop
PUJ
PWM
23h 07m
1 stop
Depart: Fri Sep 22 2017 Return: Tue Sep 26 2017 Trip spans 5 days
Major Airline
Major Airline
PWM
AUA
9h 47m
1 stop
AUA
PWM
16h 07m
1 stop
Depart: Wed Nov 1 2017 Return: Wed Nov 15 2017 Trip spans 15 days
Delta
Delta
PWM
STI
12h 02m
1 stop
STI
PWM
16h 53m
1 stop
Depart: Fri Dec 1 2017 Return: Sat Dec 9 2017 Trip spans 9 days
American Airlines
American Airlines
PWM
AUA
22h 45m
1 stop
AUA
PWM
21h 12m
1 stop
Depart: Tue Nov 14 2017 Return: Mon Nov 20 2017 Trip spans 7 days
Major Airline
Major Airline
PWM
AUA
24h 02m
1 stop
AUA
PWM
26h 40m
1 stop
Depart: Fri Sep 8 2017 Return: Fri Sep 15 2017 Trip spans 8 days
Delta
Delta
PWM
SJU
8h 52m
1 stop
SJU
PWM
7h 45m
1 stop
Depart: Wed Oct 11 2017 Return: Wed Oct 18 2017 Trip spans 8 days
American Airlines
American Airlines
PWM
PUJ
22h 35m
1 stop
PUJ
PWM
23h 07m
1 stop
Depart: Fri Oct 20 2017 Return: Sun Oct 22 2017 Trip spans 3 days
Major Airline
Major Airline
PWM
STT
16h 51m
1 stop
STT
PWM
23h 13m
1 stop
Depart: Wed Jul 5 2017 Return: Mon Jul 10 2017 Trip spans 6 days
Delta
Delta
PWM
NAS
14h 17m
1 stop
NAS
PWM
9h 54m
1 stop
Depart: Fri Sep 22 2017 Return: Sat Sep 30 2017 Trip spans 9 days
Major Airline
Major Airline
PWM
GCM
10h 35m
2 stops
GCM
PWM
18h 17m
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
$318
Destination

Bridgetown
$621
Santo Domingo
$370
Nassau
$413
Providenciales
$365
San Juan
$318
Saint Thomas Island
$446
Oranjestad
$424
George Town
$409
Punta Cana
$416
Santiago de los Caballeros
$406