Find Cheap Flights from Chicago O'Hare International 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 Chicago O'Hare International to Caribbean

(Round-trip)
Depart: Tue Oct 10 2017 Return: Mon Oct 16 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Sat Sep 30 2017 Return: Fri Oct 6 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
BQN
7h 33m
1 stop
BQN
ORD
7h 50m
1 stop
Depart: Wed Feb 7 2018 Return: Wed Feb 14 2018 Trip spans 8 days
JetBlue
JetBlue
ORD
HAV
5h 45m
1 stop
HAV
ORD
9h 01m
1 stop
Depart: Sat Oct 28 2017 Return: Wed Nov 1 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
ORD
HAV
9h 45m
1 stop
HAV
ORD
8h 06m
1 stop
Depart: Wed Oct 11 2017 Return: Tue Oct 17 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Mon Oct 16 2017 Return: Mon Oct 30 2017 Trip spans 15 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Thu Oct 12 2017 Return: Fri Oct 13 2017 Trip spans 2 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Thu Oct 5 2017 Return: Wed Oct 11 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Thu Nov 2 2017 Return: Tue Nov 7 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
ORD
HAV
9h 35m
1 stop
HAV
ORD
9h 06m
1 stop
Depart: Mon Oct 9 2017 Return: Sun Oct 15 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Thu Feb 8 2018 Return: Sun Feb 11 2018 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 44m
1 stop
SJU
ORD
19h 20m
1 stop
Depart: Thu Oct 19 2017 Return: Tue Oct 31 2017 Trip spans 13 days
JetBlue
JetBlue
ORD
HAV
6h 00m
1 stop
HAV
ORD
8h 06m
1 stop
Depart: Thu Oct 12 2017 Return: Wed Oct 18 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Sat Oct 28 2017 Return: Thu Nov 2 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
ORD
HAV
21h 45m
1 stop
HAV
ORD
8h 06m
1 stop
Depart: Fri Oct 20 2017 Return: Sat Oct 28 2017 Trip spans 9 days
JetBlue
JetBlue
ORD
HAV
6h 00m
1 stop
HAV
ORD
8h 54m
1 stop
Depart: Wed Oct 4 2017 Return: Sat Oct 7 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
SJU
18h 48m
1 stop
SJU
ORD
8h 35m
1 stop
Depart: Tue Oct 17 2017 Return: Mon Oct 23 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Sat Sep 30 2017 Return: Wed Oct 11 2017 Trip spans 12 days
Multiple Airlines
Multiple Airlines
ORD
SJU
6h 41m
1 stop
SJU
ORD
8h 35m
1 stop
Depart: Sat Oct 28 2017 Return: Tue Oct 31 2017 Trip spans 4 days
JetBlue
JetBlue
ORD
HAV
6h 00m
1 stop
HAV
ORD
8h 06m
1 stop
Depart: Sat Jan 6 2018 Return: Sat Jan 13 2018 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SJU
12h 10m
1 stop
SJU
ORD
8h 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

Chicago
$175
Destination

Aguadilla
$255
San Juan
$175
Havana
$274