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: Sun Jan 28 2018 Return: Mon Feb 5 2018 Trip spans 9 days
Multiple Airlines
Multiple Airlines
ORD
SJU
29h 11m
1 stop
SJU
ORD
31h 15m
1 stop
Depart: Wed Jan 17 2018 Return: Tue Jan 23 2018 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 48m
1 stop
SJU
ORD
32h 13m
1 stop
Depart: Thu Jan 18 2018 Return: Sat Jan 27 2018 Trip spans 10 days
JetBlue
JetBlue
ORD
HAV
5h 45m
1 stop
HAV
ORD
9h 01m
1 stop
Depart: Sun Dec 3 2017 Return: Sun Dec 10 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
HAV
10h 45m
1 stop
HAV
ORD
9h 05m
1 stop
Depart: Sun Jan 21 2018 Return: Mon Jan 29 2018 Trip spans 9 days
Multiple Airlines
Multiple Airlines
ORD
SJU
29h 11m
1 stop
SJU
ORD
31h 15m
1 stop
Depart: Wed Nov 29 2017 Return: Wed Dec 6 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 52m
1 stop
SJU
ORD
32h 28m
1 stop
Depart: Tue Dec 12 2017 Return: Thu Dec 14 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
ORD
SJU
17h 52m
1 stop
SJU
ORD
12h 29m
1 stop
Depart: Wed Dec 6 2017 Return: Sat Dec 9 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 56m
1 stop
SJU
ORD
8h 28m
1 stop
Depart: Thu Jan 18 2018 Return: Mon Jan 22 2018 Trip spans 5 days
Multiple Airlines
Multiple Airlines
ORD
SJU
11h 29m
1 stop
SJU
ORD
19h 18m
1 stop
Depart: Mon Jan 22 2018 Return: Sat Jan 27 2018 Trip spans 6 days
JetBlue
JetBlue
ORD
HAV
5h 45m
1 stop
HAV
ORD
9h 01m
1 stop
Depart: Wed Nov 1 2017 Return: Thu Nov 30 2017 Trip spans 30 days
Spirit Airlines
Spirit Airlines
ORD
SJU
30h 56m
1 stop
SJU
ORD
19h 31m
1 stop
Depart: Sun Dec 10 2017 Return: Sat Dec 16 2017 Trip spans 7 days
American Airlines
American Airlines
ORD
HAV
13h 56m
1 stop
HAV
ORD
11h 55m
1 stop
Depart: Tue Jan 23 2018 Return: Sat Jan 27 2018 Trip spans 5 days
JetBlue
JetBlue
ORD
HAV
5h 45m
1 stop
HAV
ORD
9h 01m
1 stop
Depart: Sun Dec 10 2017 Return: Fri Dec 15 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 52m
1 stop
SJU
ORD
32h 28m
1 stop
Depart: Wed Jan 17 2018 Return: Mon Jan 29 2018 Trip spans 13 days
American Airlines
American Airlines
ORD
HAV
6h 15m
1 stop
HAV
ORD
11h 57m
1 stop
Depart: Wed Nov 1 2017 Return: Fri Dec 1 2017 Trip spans 31 days
Multiple Airlines
Multiple Airlines
ORD
SJU
6h 56m
1 stop
SJU
ORD
14h 40m
1 stop
Depart: Wed Jan 17 2018 Return: Sat Jan 27 2018 Trip spans 11 days
JetBlue
JetBlue
ORD
HAV
5h 45m
1 stop
HAV
ORD
9h 01m
1 stop
Depart: Wed Nov 29 2017 Return: Tue Dec 12 2017 Trip spans 14 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 52m
1 stop
SJU
ORD
8h 28m
1 stop
Depart: Thu Jan 18 2018 Return: Mon Jan 29 2018 Trip spans 12 days
American Airlines
American Airlines
ORD
HAV
6h 15m
1 stop
HAV
ORD
7h 23m
1 stop
Depart: Mon Dec 4 2017 Return: Tue Dec 5 2017 Trip spans 2 days
Multiple Airlines
Multiple Airlines
ORD
SJU
22h 34m
1 stop
SJU
ORD
15h 15m
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
$208
Destination

San Juan
$208
Havana
$265