Find Deals on 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
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 to Caribbean

(Round-trip)
Depart: Thu Feb 9 2017 Return: Mon Feb 13 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
HAV
25h 03m
1 stop
HAV
ORD
9h 17m
1 stop
Depart: Tue Jan 31 2017 Return: Wed Feb 8 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
SJU
8h 26m
nonstop
SJU
ORD
8h 42m
nonstop
Depart: Wed Jan 11 2017 Return: Mon Jan 16 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
SJU
23h 29m
1 stop
SJU
ORD
24h 22m
1 stop
Depart: Thu Mar 2 2017 Return: Tue Mar 7 2017 Trip spans 6 days
Copa Airlines
Copa Airlines
ORD
HAV
27h 10m
1 stop
HAV
ORD
16h 25m
1 stop
Depart: Tue Jan 24 2017 Return: Tue Jan 31 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
11h 56m
2 stops
SJU
MDW
14h 22m
2 stops
Depart: Sat Feb 11 2017 Return: Sat Feb 18 2017 Trip spans 8 days
United
United
ORD
SJU
4h 30m
nonstop
SJU
ORD
5h 05m
nonstop
Depart: Tue Apr 4 2017 Return: Wed Apr 5 2017 Trip spans 2 days
American Airlines
American Airlines
ORD
SJU
4h 55m
nonstop
SJU
ORD
5h 02m
nonstop
Depart: Wed Jan 18 2017 Return: Thu Jan 26 2017 Trip spans 9 days
Air Canada
Air Canada
ORD
POS
17h 25m
1 stop
POS
ORD
16h 45m
1 stop
Depart: Tue Dec 13 2016 Return: Tue Dec 20 2016 Trip spans 8 days
Frontier
Frontier
ORD
PUJ
4h 46m
nonstop
PUJ
ORD
5h 12m
nonstop
Depart: Mon Feb 6 2017 Return: Mon Feb 13 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
BQN
18h 00m
1 stop
BQN
ORD
20h 54m
1 stop
Depart: Thu Feb 9 2017 Return: Tue Feb 14 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
SJU
10h 59m
nonstop
SJU
ORD
9h 49m
nonstop
Depart: Tue Jan 24 2017 Return: Fri Feb 3 2017 Trip spans 11 days
Spirit Airlines
Spirit Airlines
ORD
HAV
10h 30m
1 stop
HAV
ORD
6h 12m
1 stop
Depart: Wed Jan 25 2017 Return: Tue Jan 31 2017 Trip spans 7 days
Avianca
Avianca
ORD
CUR
25h 07m
2 stops
CUR
ORD
20h 03m
2 stops
Depart: Thu Feb 2 2017 Return: Wed Feb 8 2017 Trip spans 7 days
JetBlue
JetBlue
ORD
SJU
10h 19m
1 stop
SJU
ORD
9h 49m
1 stop
Depart: Fri Jun 2 2017 Return: Tue Jun 6 2017 Trip spans 5 days
Copa Airlines
Copa Airlines
ORD
HAV
15h 10m
1 stop
HAV
ORD
16h 27m
1 stop
Depart: Mon Feb 6 2017 Return: Tue Feb 14 2017 Trip spans 9 days
Delta
Delta
MDW
SJU
13h 15m
2 stops
SJU
MDW
16h 29m
2 stops
Depart: Thu Apr 27 2017 Return: Thu May 4 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
HAV
7h 54m
1 stop
HAV
ORD
7h 29m
1 stop
Depart: Tue Dec 6 2016 Return: Sun Dec 25 2016 Trip spans 20 days
Major Airline
Major Airline
ORD
SJU
6h 53m
nonstop
SJU
ORD
7h 16m
nonstop
Depart: Wed Apr 5 2017 Return: Thu Apr 13 2017 Trip spans 9 days
American Airlines
American Airlines
ORD
SJU
4h 55m
nonstop
SJU
ORD
5h 02m
nonstop
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
* 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 $224
only $287
Destination

Aguadilla
$243
San Juan
$253
Willemstad
$552
Punta Cana
$365
Havana
$224
Piarco
$351