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 Nov 11 2017 Return: Sat Nov 18 2017 Trip spans 8 days
United
United
PWM
PLS
6h 55m
1 stop
PLS
PWM
20h 53m
1 stop
Depart: Fri Nov 24 2017 Return: Fri Dec 1 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
PWM
PLS
29h 15m
1 stop
PLS
PWM
8h 27m
1 stop
Depart: Fri Dec 1 2017 Return: Sun Dec 10 2017 Trip spans 10 days
American Airlines
American Airlines
PWM
SJU
6h 34m
1 stop
SJU
PWM
10h 42m
2 stops
Depart: Tue Nov 14 2017 Return: Sun Nov 19 2017 Trip spans 6 days
Delta
Delta
PWM
SXM
19h 01m
2 stops
SXM
PWM
9h 00m
1 stop
Depart: Sat Jan 20 2018 Return: Thu Feb 1 2018 Trip spans 13 days
JetBlue
JetBlue
PWM
SDQ
12h 23m
1 stop
SDQ
PWM
8h 04m
1 stop
Depart: Mon Nov 20 2017 Return: Wed Nov 29 2017 Trip spans 10 days
United
United
PWM
NAS
6h 52m
1 stop
NAS
PWM
7h 32m
1 stop
Depart: Fri Nov 24 2017 Return: Wed Nov 29 2017 Trip spans 6 days
United
United
PWM
NAS
19h 12m
1 stop
NAS
PWM
7h 32m
1 stop
Depart: Tue Nov 7 2017 Return: Sat Nov 11 2017 Trip spans 5 days
American Airlines
American Airlines
PWM
SJU
9h 00m
2 stops
SJU
PWM
9h 59m
2 stops
Depart: Fri Jan 26 2018 Return: Wed Jan 31 2018 Trip spans 6 days
Delta
Delta
PWM
MBJ
17h 06m
1 stop
MBJ
PWM
9h 16m
1 stop
Depart: Tue Dec 12 2017 Return: Wed Dec 20 2017 Trip spans 9 days
United
United
PWM
NAS
6h 55m
1 stop
NAS
PWM
9h 14m
1 stop
Depart: Mon Jan 15 2018 Return: Thu Feb 1 2018 Trip spans 18 days
JetBlue
JetBlue
PWM
SDQ
9h 34m
1 stop
SDQ
PWM
8h 04m
1 stop
Depart: Tue Nov 14 2017 Return: Tue Dec 26 2017 Trip spans 43 days
Multiple Airlines
Multiple Airlines
PWM
STT
9h 55m
2 stops
STT
PWM
14h 50m
2 stops
Depart: Sat Feb 10 2018 Return: Thu Feb 15 2018 Trip spans 6 days
American Airlines
American Airlines
PWM
MBJ
11h 17m
1 stop
MBJ
PWM
8h 48m
1 stop
Depart: Tue Nov 28 2017 Return: Sat Dec 2 2017 Trip spans 5 days
Delta
Delta
PWM
AUA
8h 25m
1 stop
AUA
PWM
8h 29m
1 stop
Depart: Mon Dec 11 2017 Return: Wed Dec 20 2017 Trip spans 10 days
United
United
PWM
NAS
22h 25m
2 stops
NAS
PWM
9h 14m
1 stop
Depart: Sun Jan 14 2018 Return: Sun Jan 28 2018 Trip spans 15 days
JetBlue
JetBlue
PWM
SDQ
9h 05m
1 stop
SDQ
PWM
9h 38m
1 stop
Depart: Tue Nov 14 2017 Return: Wed Dec 27 2017 Trip spans 44 days
Multiple Airlines
Multiple Airlines
PWM
STT
9h 55m
2 stops
STT
PWM
14h 50m
2 stops
Depart: Tue Dec 12 2017 Return: Sun Dec 17 2017 Trip spans 6 days
United
United
PWM
NAS
6h 55m
1 stop
NAS
PWM
26h 08m
1 stop
Depart: Sat Jan 6 2018 Return: Fri Jan 12 2018 Trip spans 7 days
American Airlines
American Airlines
PWM
POP
24h 20m
2 stops
POP
PWM
20h 10m
2 stops
Depart: Sat Jan 13 2018 Return: Sat Jan 20 2018 Trip spans 8 days
Delta
Delta
PWM
PUJ
13h 57m
1 stop
PUJ
PWM
13h 23m
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
$356
Destination

Santo Domingo
$448
Nassau
$357
Providenciales
$356
San Juan
$386
Saint Thomas Island
$469
Simpson Bay
$425
San Felipe de Puerto Plata
$450
Oranjestad
$434
Montego Bay
$433
Punta Cana
$467