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.
Compare vs. KAYAK all | none

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago to Caribbean

(Round-trip)
Depart: Tue May 16 2017 Return: Tue May 23 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
HAV
5h 25m
1 stop
HAV
ORD
12h 19m
1 stop
Depart: Tue Jul 11 2017 Return: Wed Jul 19 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
HAV
6h 18m
1 stop
HAV
ORD
13h 27m
1 stop
Depart: Mon Aug 7 2017 Return: Fri Aug 11 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
HAV
6h 18m
1 stop
HAV
ORD
8h 27m
1 stop
Depart: Mon Jun 12 2017 Return: Fri Jun 16 2017 Trip spans 5 days
Delta
Delta
MDW
HAV
15h 42m
1 stop
HAV
MDW
9h 27m
1 stop
Depart: Sat May 6 2017 Return: Wed May 10 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
PUJ
4h 30m
nonstop
PUJ
ORD
17h 50m
1 stop
Depart: Wed May 3 2017 Return: Tue May 9 2017 Trip spans 7 days
Air Canada
Air Canada
ORD
POS
17h 40m
1 stop
POS
ORD
18h 18m
1 stop
Depart: Fri Jul 14 2017 Return: Sat Jul 15 2017 Trip spans 2 days
United
United
ORD
SJU
4h 45m
nonstop
SJU
ORD
5h 10m
nonstop
Depart: Sun Sep 10 2017 Return: Sun Sep 17 2017 Trip spans 8 days
Copa Airlines
Copa Airlines
ORD
PUJ
19h 49m
1 stop
PUJ
ORD
25h 26m
1 stop
Depart: Fri Jun 23 2017 Return: Wed Jun 28 2017 Trip spans 6 days
Frontier
Frontier
ORD
PUJ
4h 42m
nonstop
PUJ
ORD
5h 14m
nonstop
Depart: Sun Jun 18 2017 Return: Sun Jun 25 2017 Trip spans 8 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Tue Aug 1 2017 Return: Wed Aug 9 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
HAV
10h 25m
2 stops
HAV
ORD
15h 50m
2 stops
Depart: Sun Sep 3 2017 Return: Sun Sep 10 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
7h 08m
1 stop
Depart: Fri Oct 20 2017 Return: Sat Nov 4 2017 Trip spans 16 days
Spirit Airlines
Spirit Airlines
ORD
BQN
7h 48m
1 stop
BQN
ORD
7h 54m
1 stop
Depart: Wed May 10 2017 Return: Tue May 16 2017 Trip spans 7 days
JetBlue
JetBlue
ORD
NAS
10h 40m
1 stop
NAS
ORD
11h 58m
1 stop
Depart: Sat May 6 2017 Return: Thu May 11 2017 Trip spans 6 days
American Airlines
American Airlines
ORD
PUJ
19h 54m
1 stop
PUJ
ORD
18h 52m
1 stop
Depart: Mon May 15 2017 Return: Fri May 19 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
HAV
30h 00m
1 stop
HAV
ORD
19h 22m
1 stop
Depart: Mon May 15 2017 Return: Wed May 24 2017 Trip spans 10 days
Delta
Delta
MDW
HAV
17h 25m
2 stops
HAV
MDW
10h 15m
2 stops
Depart: Thu Sep 7 2017 Return: Mon Sep 11 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 51m
1 stop
SJU
ORD
8h 36m
1 stop
Depart: Tue May 9 2017 Return: Wed May 17 2017 Trip spans 9 days
JetBlue
JetBlue
ORD
SJU
8h 30m
1 stop
SJU
ORD
14h 10m
1 stop
Depart: Mon May 22 2017 Return: Tue May 30 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
HAV
6h 26m
1 stop
HAV
ORD
8h 33m
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.

^ The fares displayed in KAYAK ads found on other sites include all taxes and fees for economy class travel and were found by KAYAK users in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.
Airports
Origin

Chicago
only $247
only $328
Destination

Aguadilla
$331
Nassau
$333
San Juan
$334
George Town
$460
Punta Cana
$332
Havana
$247
Piarco
$351