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: Tue Sep 19 2017 Return: Tue Sep 26 2017 Trip spans 8 days
Major Airline
Major Airline
PWM
SJU
8h 49m
1 stop
SJU
PWM
8h 01m
1 stop
Depart: Thu Jun 15 2017 Return: Mon Jun 19 2017 Trip spans 5 days
Delta
Delta
PWM
NAS
6h 07m
1 stop
NAS
PWM
10h 57m
1 stop
Depart: Tue Nov 21 2017 Return: Wed Nov 29 2017 Trip spans 9 days
American Airlines
American Airlines
PWM
NAS
21h 13m
1 stop
NAS
PWM
19h 05m
1 stop
Depart: Fri Nov 3 2017 Return: Fri Nov 10 2017 Trip spans 8 days
JetBlue
JetBlue
PWM
SJU
8h 18m
1 stop
SJU
PWM
9h 43m
1 stop
Depart: Mon Nov 20 2017 Return: Wed Nov 22 2017 Trip spans 3 days
United
United
PWM
PUJ
8h 35m
1 stop
PUJ
PWM
23h 25m
1 stop
Depart: Mon Jul 10 2017 Return: Tue Jul 18 2017 Trip spans 9 days
Major Airline
Major Airline
PWM
NAS
13h 31m
2 stops
NAS
PWM
22h 18m
2 stops
Depart: Sat Oct 28 2017 Return: Fri Nov 3 2017 Trip spans 7 days
American Airlines
American Airlines
PWM
PLS
23h 30m
1 stop
PLS
PWM
22h 22m
1 stop
Depart: Tue Aug 29 2017 Return: Mon Sep 4 2017 Trip spans 7 days
JetBlue
JetBlue
PWM
SJU
9h 35m
1 stop
SJU
PWM
17h 46m
2 stops
Depart: Mon Nov 6 2017 Return: Fri Nov 17 2017 Trip spans 12 days
Delta
Delta
PWM
STI
12h 02m
1 stop
STI
PWM
16h 53m
1 stop
Depart: Thu Jun 8 2017 Return: Sun Jun 11 2017 Trip spans 4 days
Major Airline
Major Airline
PWM
SJU
6h 34m
2 stops
SJU
PWM
18h 31m
2 stops
Depart: Mon Aug 28 2017 Return: Sat Sep 2 2017 Trip spans 6 days
United
United
PWM
AUA
18h 30m
1 stop
AUA
PWM
22h 14m
2 stops
Depart: Sun Oct 15 2017 Return: Sat Oct 21 2017 Trip spans 7 days
American Airlines
American Airlines
PWM
SJU
6h 20m
1 stop
SJU
PWM
6h 27m
1 stop
Depart: Tue Sep 26 2017 Return: Tue Oct 3 2017 Trip spans 8 days
Delta
Delta
PWM
AUA
7h 25m
1 stop
AUA
PWM
8h 28m
1 stop
Depart: Sat Sep 30 2017 Return: Sat Oct 7 2017 Trip spans 8 days
United
United
PWM
MBJ
7h 00m
1 stop
MBJ
PWM
15h 28m
1 stop
Depart: Tue Sep 19 2017 Return: Tue Sep 26 2017 Trip spans 8 days
American Airlines
American Airlines
PWM
SXM
25h 19m
2 stops
SXM
PWM
20h 17m
2 stops
Depart: Sat Jul 15 2017 Return: Fri Jul 21 2017 Trip spans 7 days
Major Airline
Major Airline
PWM
NAS
9h 45m
2 stops
NAS
PWM
13h 06m
2 stops
Depart: Mon Nov 13 2017 Return: Mon Nov 20 2017 Trip spans 8 days
American Airlines
American Airlines
PWM
AUA
24h 40m
1 stop
AUA
PWM
23h 25m
1 stop
Depart: Sun Oct 8 2017 Return: Sun Oct 15 2017 Trip spans 8 days
Major Airline
Major Airline
PWM
SXM
21h 27m
1 stop
SXM
PWM
9h 43m
1 stop
Depart: Sat Oct 28 2017 Return: Sat Nov 4 2017 Trip spans 8 days
American Airlines
American Airlines
PWM
PUJ
24h 40m
1 stop
PUJ
PWM
24h 07m
1 stop
Depart: Thu Sep 7 2017 Return: Tue Sep 12 2017 Trip spans 6 days
Delta
Delta
PWM
AUA
8h 40m
1 stop
AUA
PWM
7h 55m
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
$294
Destination

Nassau
$329
Providenciales
$371
San Juan
$294
Simpson Bay
$419
Oranjestad
$419
Montego Bay
$431
Punta Cana
$384
Santiago de los Caballeros
$400