Find Deals on 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
Students
under 26
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 Chicago O'Hare International to Caribbean

(Round-trip)
Depart: Tue Jan 31 2017 Return: Wed Feb 8 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 53m
1 stop
SJU
ORD
7h 17m
1 stop
Depart: Mon Apr 10 2017 Return: Tue Apr 11 2017 Trip spans 2 days
JetBlue
JetBlue
ORD
HAV
7h 15m
1 stop
HAV
ORD
7h 25m
1 stop
Depart: Sat Jan 28 2017 Return: Tue Feb 7 2017 Trip spans 11 days
Major Airline
Major Airline
ORD
BQN
17h 59m
1 stop
BQN
ORD
8h 38m
1 stop
Depart: Sat Dec 31 2016 Return: Sat Jan 14 2017 Trip spans 15 days
United
United
ORD
SJU
4h 35m
nonstop
SJU
ORD
5h 05m
nonstop
Depart: Wed Feb 22 2017 Return: Thu Mar 2 2017 Trip spans 9 days
American Airlines
American Airlines
ORD
SJU
8h 59m
1 stop
SJU
ORD
5h 27m
nonstop
Depart: Fri Jun 23 2017 Return: Wed Jun 28 2017 Trip spans 6 days
Copa Airlines
Copa Airlines
ORD
HAV
9h 09m
1 stop
HAV
ORD
16h 58m
1 stop
Depart: Sat Apr 15 2017 Return: Sat Apr 22 2017 Trip spans 8 days
Delta
Delta
ORD
HAV
15h 30m
1 stop
HAV
ORD
9h 19m
1 stop
Depart: Tue Dec 13 2016 Return: Tue Dec 27 2016 Trip spans 15 days
Frontier
Frontier
ORD
PUJ
4h 46m
nonstop
PUJ
ORD
5h 12m
nonstop
Depart: Tue Dec 6 2016 Return: Sun Dec 11 2016 Trip spans 6 days
Air Canada
Air Canada
ORD
PLS
15h 40m
1 stop
PLS
ORD
19h 40m
1 stop
Depart: Sat Feb 18 2017 Return: Sat Feb 25 2017 Trip spans 8 days
Aeromexico
Aeromexico
ORD
SDQ
14h 16m
1 stop
SDQ
ORD
27h 08m
2 stops
Depart: Tue Feb 28 2017 Return: Tue Mar 7 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SJU
8h 28m
nonstop
SJU
ORD
14h 48m
nonstop
Depart: Sun Mar 5 2017 Return: Tue Mar 7 2017 Trip spans 3 days
JetBlue
JetBlue
ORD
SJU
8h 28m
1 stop
SJU
ORD
9h 49m
1 stop
Depart: Thu Jan 19 2017 Return: Wed Jan 25 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
STT
9h 12m
1 stop
STT
ORD
7h 40m
1 stop
Depart: Wed Apr 26 2017 Return: Sun Apr 30 2017 Trip spans 5 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
4h 00m
nonstop
Depart: Tue Feb 7 2017 Return: Tue Feb 14 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
STT
9h 12m
1 stop
STT
ORD
7h 38m
1 stop
Depart: Sun Feb 19 2017 Return: Tue Feb 28 2017 Trip spans 10 days
Avianca
Avianca
ORD
CUR
25h 07m
2 stops
CUR
ORD
20h 03m
2 stops
Depart: Fri Jan 27 2017 Return: Fri Feb 3 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
AUA
22h 03m
1 stop
AUA
ORD
22h 00m
1 stop
Depart: Thu Feb 23 2017 Return: Thu Mar 2 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
AUA
26h 58m
1 stop
AUA
ORD
8h 40m
1 stop
Depart: Sat Feb 4 2017 Return: Sat Feb 11 2017 Trip spans 8 days
United
United
ORD
SJU
4h 30m
nonstop
SJU
ORD
5h 05m
nonstop
Depart: Thu Jan 12 2017 Return: Tue Jan 17 2017 Trip spans 6 days
JetBlue
JetBlue
ORD
SJU
13h 07m
1 stop
SJU
ORD
29h 07m
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
$191
Destination

Aguadilla
$243
Santo Domingo
$478
Providenciales
$444
San Juan
$191
Saint Thomas Island
$249
Oranjestad
$254
Willemstad
$554
George Town
$534
Punta Cana
$375
Havana
$233