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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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Portland to Caribbean

(Round-trip)
Depart: Tue Feb 6 2018 Return: Wed Feb 7 2018 Trip spans 2 days
American Airlines
American Airlines
PWM
SJU
9h 34m
2 stops
SJU
PWM
6h 27m
1 stop
Depart: Sat Jan 20 2018 Return: Tue Jan 23 2018 Trip spans 4 days
Delta
Delta
PWM
SJU
7h 59m
1 stop
SJU
PWM
6h 12m
1 stop
Depart: Sat Jan 27 2018 Return: Sat Feb 3 2018 Trip spans 8 days
United
United
PWM
SJU
17h 13m
2 stops
SJU
PWM
14h 10m
2 stops
Depart: Wed Oct 11 2017 Return: Mon Oct 16 2017 Trip spans 6 days
JetBlue
JetBlue
PWM
PLS
8h 39m
1 stop
PLS
PWM
8h 33m
1 stop
Depart: Fri Sep 29 2017 Return: Tue Oct 3 2017 Trip spans 5 days
Delta
Delta
PWM
SJU
6h 08m
1 stop
SJU
PWM
9h 30m
1 stop
Depart: Thu Aug 31 2017 Return: Sat Sep 9 2017 Trip spans 10 days
United
United
PWM
BQN
16h 59m
1 stop
BQN
PWM
9h 53m
1 stop
Depart: Sun Jan 14 2018 Return: Tue Jan 23 2018 Trip spans 10 days
American Airlines
American Airlines
PWM
NAS
5h 45m
1 stop
NAS
PWM
5h 36m
1 stop
Depart: Fri Sep 1 2017 Return: Sat Sep 9 2017 Trip spans 9 days
United
United
PWM
BQN
16h 59m
1 stop
BQN
PWM
14h 10m
1 stop
Depart: Sat Feb 3 2018 Return: Mon Feb 12 2018 Trip spans 10 days
American Airlines
American Airlines
PWM
NAS
5h 48m
1 stop
NAS
PWM
7h 21m
1 stop
Depart: Sat Sep 16 2017 Return: Sat Sep 23 2017 Trip spans 8 days
Delta
Delta
PWM
NAS
6h 04m
1 stop
NAS
PWM
9h 59m
1 stop
Depart: Wed Oct 25 2017 Return: Fri Oct 27 2017 Trip spans 3 days
Delta
Delta
PWM
NAS
5h 56m
1 stop
NAS
PWM
15h 50m
1 stop
Depart: Tue Feb 6 2018 Return: Sat Feb 17 2018 Trip spans 12 days
United
United
PWM
NAS
20h 36m
1 stop
NAS
PWM
7h 33m
1 stop
Depart: Wed Feb 28 2018 Return: Tue Mar 13 2018 Trip spans 13 days
American Airlines
American Airlines
PWM
BGI
15h 34m
2 stops
BGI
PWM
21h 00m
2 stops
Depart: Fri Oct 27 2017 Return: Fri Nov 3 2017 Trip spans 8 days
Delta
Delta
PWM
NAS
16h 12m
1 stop
NAS
PWM
15h 50m
1 stop
Depart: Sat Nov 11 2017 Return: Sat Nov 18 2017 Trip spans 8 days
United
United
PWM
PLS
9h 25m
1 stop
PLS
PWM
44h 09m
2 stops
Depart: Fri Jan 5 2018 Return: Tue Jan 9 2018 Trip spans 5 days
Delta
Delta
PWM
NAS
6h 05m
1 stop
NAS
PWM
15h 25m
1 stop
Depart: Sat Nov 4 2017 Return: Mon Nov 13 2017 Trip spans 10 days
American Airlines
American Airlines
PWM
GCM
23h 10m
1 stop
GCM
PWM
19h 54m
2 stops
Depart: Wed Nov 15 2017 Return: Wed Nov 22 2017 Trip spans 8 days
JetBlue
JetBlue
PWM
STI
8h 48m
1 stop
STI
PWM
10h 24m
1 stop
Depart: Mon Jan 29 2018 Return: Wed Feb 7 2018 Trip spans 10 days
United
United
PWM
PUJ
16h 25m
1 stop
PUJ
PWM
8h 32m
1 stop
Depart: Sun Jan 14 2018 Return: Mon Jan 22 2018 Trip spans 9 days
American Airlines
American Airlines
PWM
SXM
7h 10m
1 stop
SXM
PWM
7h 13m
1 stop
* 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
$288
Destination

Aguadilla
$337
Bridgetown
$368
Nassau
$354
Providenciales
$373
San Juan
$288
Simpson Bay
$419
George Town
$417
Punta Cana
$386
Santiago de los Caballeros
$558