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 Aug 29 2017 Return: Tue Sep 5 2017 Trip spans 8 days
Frontier
Frontier
ORD
SJU
17h 40m
1 stop
SJU
ORD
17h 37m
1 stop
Depart: Wed Aug 23 2017 Return: Sun Aug 27 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
BQN
8h 14m
1 stop
BQN
ORD
8h 54m
1 stop
Depart: Tue Aug 29 2017 Return: Sat Sep 9 2017 Trip spans 12 days
JetBlue
JetBlue
ORD
HAV
5h 45m
1 stop
HAV
ORD
8h 54m
1 stop
Depart: Mon Aug 21 2017 Return: Fri Sep 1 2017 Trip spans 12 days
American Airlines
American Airlines
ORD
HAV
15h 50m
1 stop
HAV
ORD
12h 38m
1 stop
Depart: Thu Aug 24 2017 Return: Mon Aug 28 2017 Trip spans 5 days
Copa Airlines
Copa Airlines
ORD
HAV
25h 20m
1 stop
HAV
ORD
17h 00m
1 stop
Depart: Mon Sep 11 2017 Return: Tue Sep 19 2017 Trip spans 9 days
Air Canada
Air Canada
ORD
POS
25h 00m
1 stop
POS
ORD
9h 04m
1 stop
Depart: Sat Jan 13 2018 Return: Thu Jan 18 2018 Trip spans 6 days
United
United
ORD
SJU
4h 35m
nonstop
SJU
ORD
5h 10m
nonstop
Depart: Thu Aug 31 2017 Return: Mon Sep 4 2017 Trip spans 5 days
Aeromexico
Aeromexico
ORD
SDQ
22h 26m
1 stop
SDQ
ORD
28h 49m
1 stop
Depart: Fri Dec 1 2017 Return: Fri Dec 15 2017 Trip spans 15 days
Bahamasair
Bahamasair
ORD
NAS
3h 30m
nonstop
NAS
ORD
3h 30m
nonstop
Depart: Wed Jan 24 2018 Return: Sun Jan 28 2018 Trip spans 5 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Wed Nov 1 2017 Return: Sat Nov 11 2017 Trip spans 11 days
Delta
Delta
ORD
STI
15h 23m
1 stop
STI
ORD
16h 20m
1 stop
Depart: Thu Sep 21 2017 Return: Mon Sep 25 2017 Trip spans 5 days
Avianca
Avianca
ORD
CUR
25h 07m
2 stops
CUR
ORD
20h 09m
2 stops
Depart: Tue Sep 12 2017 Return: Tue Sep 19 2017 Trip spans 8 days
Frontier
Frontier
ORD
SJU
17h 39m
1 stop
SJU
ORD
18h 00m
1 stop
Depart: Sat Oct 21 2017 Return: Fri Oct 27 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
BQN
7h 33m
1 stop
BQN
ORD
7h 50m
1 stop
Depart: Wed Sep 6 2017 Return: Mon Sep 11 2017 Trip spans 6 days
JetBlue
JetBlue
ORD
HAV
6h 00m
1 stop
HAV
ORD
8h 54m
1 stop
Depart: Wed Sep 13 2017 Return: Mon Sep 18 2017 Trip spans 6 days
Frontier
Frontier
ORD
SJU
17h 39m
1 stop
SJU
ORD
18h 00m
1 stop
Depart: Sat Sep 16 2017 Return: Wed Sep 20 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
HAV
6h 00m
1 stop
HAV
ORD
8h 54m
1 stop
Depart: Thu Jan 4 2018 Return: Wed Jan 10 2018 Trip spans 7 days
American Airlines
American Airlines
ORD
HAV
12h 05m
1 stop
HAV
ORD
12h 32m
1 stop
Depart: Sat Oct 14 2017 Return: Sun Oct 22 2017 Trip spans 9 days
Copa Airlines
Copa Airlines
ORD
HAV
20h 05m
1 stop
HAV
ORD
13h 10m
1 stop
Depart: Fri Aug 18 2017 Return: Sun Aug 27 2017 Trip spans 10 days
Spirit Airlines
Spirit Airlines
ORD
BQN
8h 14m
1 stop
BQN
ORD
8h 54m
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
$279
Destination

Aguadilla
$280
Santo Domingo
$399
Nassau
$401
San Juan
$279
Willemstad
$553
George Town
$419
Havana
$292
Santiago de los Caballeros
$444
Piarco
$352