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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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: Mon Sep 11 2017 Return: Sun Sep 17 2017 Trip spans 7 days
JetBlue
JetBlue
ORD
BQN
16h 58m
1 stop
BQN
ORD
21h 59m
1 stop
Depart: Fri Aug 18 2017 Return: Sat Aug 26 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
HAV
6h 53m
1 stop
HAV
ORD
7h 53m
1 stop
Depart: Fri Oct 27 2017 Return: Sat Oct 28 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
BQN
7h 36m
1 stop
BQN
ORD
7h 50m
1 stop
Depart: Tue Oct 17 2017 Return: Tue Oct 24 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
STT
6h 45m
1 stop
STT
ORD
8h 07m
1 stop
Depart: Wed Sep 20 2017 Return: Tue Sep 26 2017 Trip spans 7 days
Air Canada
Air Canada
ORD
POS
25h 20m
2 stops
POS
ORD
17h 14m
1 stop
Depart: Thu Sep 28 2017 Return: Tue Oct 3 2017 Trip spans 6 days
United
United
ORD
SJU
4h 45m
nonstop
SJU
ORD
5h 10m
nonstop
Depart: Sat May 27 2017 Return: Sat Jun 3 2017 Trip spans 8 days
Aeromexico
Aeromexico
ORD
HAV
30h 05m
1 stop
HAV
ORD
24h 00m
1 stop
Depart: Wed Jul 5 2017 Return: Wed Jul 12 2017 Trip spans 8 days
Delta
Delta
ORD
PUJ
12h 09m
2 stops
PUJ
ORD
16h 40m
2 stops
Depart: Fri Nov 24 2017 Return: Sat Dec 2 2017 Trip spans 9 days
Copa Airlines
Copa Airlines
ORD
STI
29h 15m
1 stop
STI
ORD
22h 16m
1 stop
Depart: Sun Jun 4 2017 Return: Sun Jun 11 2017 Trip spans 8 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Sun Oct 15 2017 Return: Sat Oct 21 2017 Trip spans 7 days
Avianca
Avianca
ORD
CUR
25h 07m
2 stops
CUR
ORD
20h 09m
2 stops
Depart: Wed Aug 30 2017 Return: Tue Sep 5 2017 Trip spans 7 days
Major Airline
Major Airline
ORD
BQN
11h 40m
1 stop
BQN
ORD
8h 15m
1 stop
Depart: Wed Nov 1 2017 Return: Wed Nov 8 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
NAS
10h 04m
1 stop
NAS
ORD
15h 20m
1 stop
Depart: Thu Oct 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 53m
1 stop
SJU
ORD
6h 44m
1 stop
Depart: Wed Oct 4 2017 Return: Tue Oct 10 2017 Trip spans 7 days
Air Canada
Air Canada
ORD
POS
25h 20m
2 stops
POS
ORD
13h 39m
1 stop
Depart: Mon Jun 12 2017 Return: Mon Jun 19 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
HAV
15h 40m
1 stop
HAV
ORD
12h 44m
1 stop
Depart: Sun Jun 25 2017 Return: Mon Jun 26 2017 Trip spans 2 days
Major Airline
Major Airline
ORD
HAV
12h 45m
1 stop
HAV
ORD
12h 30m
1 stop
Depart: Fri Oct 20 2017 Return: Tue Oct 24 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 53m
1 stop
SJU
ORD
8h 32m
1 stop
Depart: Wed Oct 25 2017 Return: Tue Oct 31 2017 Trip spans 7 days
JetBlue
JetBlue
ORD
NAS
10h 08m
1 stop
NAS
ORD
7h 57m
1 stop
Depart: Sun Nov 12 2017 Return: Fri Nov 17 2017 Trip spans 6 days
United
United
ORD
PUJ
4h 30m
nonstop
PUJ
ORD
5h 10m
nonstop
* 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
$305
Destination

Aguadilla
$305
Nassau
$335
San Juan
$336
Saint Thomas Island
$345
Willemstad
$568
George Town
$450
Punta Cana
$400
Havana
$325
Santiago de los Caballeros
$434
Piarco
$351