Find Cheap Flights from Chicago 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 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: Tue Sep 5 2017 Return: Mon Sep 11 2017 Trip spans 7 days
Major Airline
Major Airline
ORD
HAV
12h 45m
1 stop
HAV
ORD
12h 30m
1 stop
Depart: Thu Aug 24 2017 Return: Wed Aug 30 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 56m
1 stop
SJU
ORD
8h 16m
1 stop
Depart: Mon Aug 14 2017 Return: Wed Aug 30 2017 Trip spans 17 days
Delta
Delta
MDW
HAV
15h 53m
1 stop
HAV
MDW
7h 32m
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
13h 39m
1 stop
Depart: Mon May 29 2017 Return: Wed May 31 2017 Trip spans 3 days
Aeromexico
Aeromexico
ORD
HAV
22h 50m
2 stops
HAV
ORD
17h 45m
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
Depart: Tue May 30 2017 Return: Thu Jun 1 2017 Trip spans 3 days
American Airlines
American Airlines
ORD
PUJ
15h 57m
1 stop
PUJ
ORD
12h 10m
1 stop
Depart: Fri Nov 17 2017 Return: Mon Nov 20 2017 Trip spans 4 days
Southwest
Southwest
MDW
SJU
4h 35m
nonstop
SJU
MDW
9h 00m
nonstop
Depart: Thu Jun 29 2017 Return: Mon Jul 3 2017 Trip spans 5 days
Copa Airlines
Copa Airlines
ORD
STI
23h 35m
1 stop
STI
ORD
22h 16m
1 stop
Depart: Sun Jul 2 2017 Return: Sun Jul 9 2017 Trip spans 8 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Wed Oct 4 2017 Return: Fri Oct 13 2017 Trip spans 10 days
Major Airline
Major Airline
ORD
HAV
12h 45m
1 stop
HAV
ORD
12h 55m
1 stop
Depart: Thu Sep 28 2017 Return: Tue Oct 3 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 53m
1 stop
SJU
ORD
8h 32m
1 stop
Depart: Sat Jul 1 2017 Return: Sat Jul 8 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
BQN
8h 53m
1 stop
BQN
ORD
17h 30m
2 stops
Depart: Tue Sep 5 2017 Return: Tue Sep 19 2017 Trip spans 15 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
7h 32m
1 stop
Depart: Thu Jul 13 2017 Return: Thu Jul 20 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
HAV
9h 35m
1 stop
HAV
ORD
22h 57m
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: Fri Sep 29 2017 Return: Sat Oct 7 2017 Trip spans 9 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
7h 26m
1 stop
Depart: Fri Sep 8 2017 Return: Mon Sep 11 2017 Trip spans 4 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
* 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
only $305
only $334
Destination

Aguadilla
$305
Nassau
$355
San Juan
$324
George Town
$459
Punta Cana
$400
Havana
$313
Santiago de los Caballeros
$434
Piarco
$351