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: Mon Nov 6 2017 Return: Fri Nov 10 2017 Trip spans 5 days
American Airlines
American Airlines
PDX
HAV
11h 00m
1 stop
HAV
PDX
12h 12m
1 stop
Depart: Mon Sep 11 2017 Return: Sat Sep 16 2017 Trip spans 6 days
Delta
Delta
PDX
HAV
20h 30m
2 stops
HAV
PDX
21h 01m
2 stops
Depart: Sun Oct 22 2017 Return: Wed Nov 1 2017 Trip spans 11 days
Major Airline
Major Airline
PDX
AUA
22h 29m
2 stops
AUA
PDX
37h 23m
2 stops
Depart: Sun Nov 19 2017 Return: Wed Nov 22 2017 Trip spans 4 days
United
United
PDX
PUJ
17h 55m
2 stops
PUJ
PDX
26h 57m
2 stops
Depart: Sat Jul 15 2017 Return: Mon Jul 31 2017 Trip spans 17 days
Alaska Airlines
Alaska Airlines
PDX
HAV
18h 55m
1 stop
HAV
PDX
17h 23m
1 stop
Depart: Sat Jun 17 2017 Return: Fri Jun 23 2017 Trip spans 7 days
Air Canada
Air Canada
PDX
BGI
16h 10m
2 stops
BGI
PDX
22h 20m
2 stops
Depart: Tue Oct 3 2017 Return: Sat Oct 7 2017 Trip spans 5 days
American Airlines
American Airlines
PDX
HAV
14h 00m
2 stops
HAV
PDX
13h 12m
1 stop
Depart: Sat Jun 17 2017 Return: Fri Jun 23 2017 Trip spans 7 days
JetBlue
JetBlue
PDX
PAP
12h 11m
1 stop
PAP
PDX
14h 27m
1 stop
Depart: Sat Sep 9 2017 Return: Sat Sep 16 2017 Trip spans 8 days
Delta
Delta
PDX
HAV
19h 55m
2 stops
HAV
PDX
21h 01m
2 stops
Depart: Wed Aug 9 2017 Return: Sun Aug 27 2017 Trip spans 19 days
Major Airline
Major Airline
PDX
HAV
29h 10m
2 stops
HAV
PDX
29h 59m
2 stops
Depart: Thu Aug 3 2017 Return: Wed Aug 9 2017 Trip spans 7 days
Aeromexico
Aeromexico
PDX
SDQ
19h 26m
2 stops
SDQ
PDX
18h 14m
2 stops
Depart: Sun May 28 2017 Return: Thu Jun 8 2017 Trip spans 12 days
United
United
PDX
SJU
15h 30m
2 stops
SJU
PDX
11h 45m
1 stop
Depart: Wed Sep 6 2017 Return: Tue Sep 12 2017 Trip spans 7 days
Major Airline
Major Airline
PDX
SJU
20h 17m
2 stops
SJU
PDX
21h 26m
2 stops
Depart: Wed Nov 1 2017 Return: Tue Nov 7 2017 Trip spans 7 days
Delta
Delta
PDX
HAV
19h 55m
2 stops
HAV
PDX
21h 01m
2 stops
Depart: Sun Oct 8 2017 Return: Sun Oct 15 2017 Trip spans 8 days
American Airlines
American Airlines
PDX
GCM
24h 15m
1 stop
GCM
PDX
21h 30m
1 stop
Depart: Fri Oct 27 2017 Return: Fri Nov 3 2017 Trip spans 8 days
Major Airline
Major Airline
PDX
SJU
26h 57m
2 stops
SJU
PDX
21h 26m
2 stops
Depart: Mon Jun 12 2017 Return: Sun Jun 18 2017 Trip spans 7 days
Delta
Delta
PDX
NAS
10h 59m
1 stop
NAS
PDX
13h 44m
1 stop
Depart: Sat Oct 14 2017 Return: Fri Oct 20 2017 Trip spans 7 days
American Airlines
American Airlines
PDX
NAS
12h 05m
2 stops
NAS
PDX
10h 47m
1 stop
Depart: Sun Nov 12 2017 Return: Wed Nov 15 2017 Trip spans 4 days
United
United
PDX
MBJ
11h 55m
1 stop
MBJ
PDX
11h 16m
1 stop
Depart: Mon Nov 6 2017 Return: Tue Nov 14 2017 Trip spans 9 days
Major Airline
Major Airline
PDX
NAS
14h 41m
2 stops
NAS
PDX
38h 49m
2 stops
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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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
$399
Destination

Port Au Prince
$830
Bridgetown
$698
Santo Domingo
$870
Nassau
$450
San Juan
$438
Oranjestad
$425
Montego Bay
$519
George Town
$459
Punta Cana
$439
Havana
$399