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 Jan 16 2018 Return: Tue Jan 23 2018 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 57m
1 stop
SJU
ORD
8h 14m
1 stop
Depart: Wed Feb 7 2018 Return: Tue Feb 13 2018 Trip spans 7 days
Multiple Airlines
Multiple Airlines
ORD
SJU
6h 57m
1 stop
SJU
ORD
13h 51m
1 stop
Depart: Mon Jan 22 2018 Return: Mon Jan 29 2018 Trip spans 8 days
United
United
ORD
HAV
6h 50m
1 stop
HAV
ORD
8h 09m
1 stop
Depart: Mon Jan 15 2018 Return: Wed Jan 31 2018 Trip spans 17 days
Aeromexico
Aeromexico
ORD
HAV
30h 20m
1 stop
HAV
ORD
18h 49m
2 stops
Depart: Thu Feb 1 2018 Return: Sat Feb 10 2018 Trip spans 10 days
American Airlines
American Airlines
ORD
HAV
13h 15m
1 stop
HAV
ORD
9h 07m
1 stop
Depart: Tue Jan 23 2018 Return: Tue Feb 6 2018 Trip spans 15 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 57m
1 stop
SJU
ORD
8h 14m
1 stop
Depart: Wed Jan 17 2018 Return: Wed Jan 24 2018 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
STT
9h 17m
1 stop
STT
ORD
8h 38m
1 stop
Depart: Thu Mar 1 2018 Return: Mon Mar 5 2018 Trip spans 5 days
Multiple Airlines
Multiple Airlines
ORD
STT
7h 30m
1 stop
STT
ORD
8h 03m
1 stop
Depart: Mon Mar 5 2018 Return: Thu Mar 8 2018 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
STT
9h 15m
1 stop
STT
ORD
8h 46m
1 stop
Depart: Mon Jan 15 2018 Return: Thu Jan 18 2018 Trip spans 4 days
Multiple Airlines
Multiple Airlines
ORD
SJU
6h 57m
1 stop
SJU
ORD
24h 55m
1 stop
Depart: Tue Jan 16 2018 Return: Sat Jan 20 2018 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 57m
1 stop
SJU
ORD
8h 14m
1 stop
Depart: Mon Mar 12 2018 Return: Wed Mar 14 2018 Trip spans 3 days
American Airlines
American Airlines
ORD
HAV
14h 35m
1 stop
HAV
ORD
11h 47m
1 stop
Depart: Wed Jan 17 2018 Return: Sat Jan 20 2018 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 57m
1 stop
SJU
ORD
8h 14m
1 stop
Depart: Wed Jan 31 2018 Return: Wed Feb 7 2018 Trip spans 8 days
Multiple Airlines
Multiple Airlines
ORD
STT
9h 17m
1 stop
STT
ORD
16h 51m
2 stops
Depart: Tue Mar 27 2018 Return: Tue Apr 3 2018 Trip spans 8 days
American Airlines
American Airlines
ORD
HAV
14h 35m
1 stop
HAV
ORD
12h 32m
1 stop
Depart: Thu Jan 18 2018 Return: Tue Jan 23 2018 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 57m
1 stop
SJU
ORD
8h 14m
1 stop
Depart: Sat Apr 7 2018 Return: Thu Apr 12 2018 Trip spans 6 days
American Airlines
American Airlines
ORD
HAV
14h 35m
1 stop
HAV
ORD
12h 32m
1 stop
Depart: Mon Dec 4 2017 Return: Tue Dec 12 2017 Trip spans 9 days
Multiple Airlines
Multiple Airlines
ORD
SJU
22h 34m
1 stop
SJU
ORD
10h 26m
1 stop
Depart: Sat Jan 20 2018 Return: Thu Feb 8 2018 Trip spans 20 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 57m
1 stop
SJU
ORD
8h 14m
1 stop
Depart: Sun Apr 15 2018 Return: Tue Apr 24 2018 Trip spans 10 days
American Airlines
American Airlines
ORD
HAV
6h 50m
1 stop
HAV
ORD
12h 32m
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.

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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 and someone from our team will get back to you promptly.

Airports
Origin

Chicago
$188
Destination

San Juan
$188
Saint Thomas Island
$192
Havana
$262