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: Wed Oct 11 2017 Return: Mon Oct 16 2017 Trip spans 6 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Mon Dec 11 2017 Return: Wed Dec 13 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
ORD
SJU
28h 39m
1 stop
SJU
ORD
8h 43m
1 stop
Depart: Wed Sep 6 2017 Return: Tue Sep 12 2017 Trip spans 7 days
JetBlue
JetBlue
ORD
HAV
6h 00m
1 stop
HAV
ORD
8h 54m
1 stop
Depart: Mon Nov 6 2017 Return: Mon Nov 13 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
BQN
8h 03m
1 stop
BQN
ORD
8h 39m
1 stop
Depart: Tue Feb 13 2018 Return: Sat Feb 17 2018 Trip spans 5 days
American Airlines
American Airlines
ORD
HAV
5h 33m
1 stop
HAV
ORD
8h 50m
1 stop
Depart: Fri Sep 15 2017 Return: Thu Sep 21 2017 Trip spans 7 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
7h 16m
1 stop
Depart: Fri Nov 17 2017 Return: Tue Nov 21 2017 Trip spans 5 days
Copa Airlines
Copa Airlines
ORD
HAV
27h 35m
1 stop
HAV
ORD
9h 50m
1 stop
Depart: Sun Oct 1 2017 Return: Sat Oct 7 2017 Trip spans 7 days
United
United
ORD
SJU
4h 40m
nonstop
SJU
ORD
5h 05m
nonstop
Depart: Tue Nov 28 2017 Return: Mon Dec 4 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 07m
1 stop
SJU
ORD
11h 43m
1 stop
Depart: Tue Oct 10 2017 Return: Tue Oct 17 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
HAV
6h 00m
1 stop
HAV
ORD
8h 54m
1 stop
Depart: Wed Dec 6 2017 Return: Mon Dec 11 2017 Trip spans 6 days
Frontier
Frontier
ORD
SJU
19h 07m
1 stop
SJU
ORD
11h 36m
1 stop
Depart: Tue Nov 28 2017 Return: Wed Dec 6 2017 Trip spans 9 days
Multiple Airlines
Multiple Airlines
ORD
SJU
9h 57m
1 stop
SJU
ORD
8h 58m
1 stop
Depart: Tue Dec 12 2017 Return: Tue Dec 19 2017 Trip spans 8 days
Frontier
Frontier
ORD
SJU
19h 09m
1 stop
SJU
ORD
11h 36m
1 stop
Depart: Sun Oct 1 2017 Return: Fri Oct 6 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
ORD
BQN
16h 58m
1 stop
BQN
ORD
7h 50m
1 stop
Depart: Mon Sep 11 2017 Return: Wed Sep 13 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
ORD
STT
9h 12m
1 stop
STT
ORD
8h 41m
1 stop
Depart: Mon Oct 30 2017 Return: Tue Nov 7 2017 Trip spans 9 days
JetBlue
JetBlue
ORD
PLS
7h 02m
1 stop
PLS
ORD
8h 04m
1 stop
Depart: Tue Jan 23 2018 Return: Mon Feb 5 2018 Trip spans 14 days
Frontier
Frontier
ORD
SJU
19h 09m
1 stop
SJU
ORD
11h 36m
1 stop
Depart: Tue Sep 19 2017 Return: Wed Sep 27 2017 Trip spans 9 days
Multiple Airlines
Multiple Airlines
ORD
SJU
17h 39m
1 stop
SJU
ORD
14h 03m
1 stop
Depart: Mon Sep 25 2017 Return: Sat Sep 30 2017 Trip spans 6 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
7h 14m
1 stop
Depart: Mon Nov 20 2017 Return: Thu Nov 23 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
BQN
7h 02m
1 stop
BQN
ORD
8h 39m
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 $229
only $328
Destination

Aguadilla
$268
Providenciales
$281
San Juan
$229
Saint Thomas Island
$304
Havana
$256