Find Cheap Flights from Chicago to Caribbean

Depart
Return
1 adult
Cabin Economy
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
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The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Chicago to Caribbean

(Round-trip)
Depart: Mon Sep 11 2017 Return: Sun Sep 17 2017 Trip spans 7 days
$305
Select
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
$313
Select
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
$324
Select
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
$334
Select
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
$351
Select
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
$366
Select
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
$400
Select
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
$413
Select
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
$428
Select
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
$434
Select
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
$459
Select
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
$314
Select
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
$333
Select
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
$334
Select
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
$334
Select
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
$315
Select
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
$351
Select
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
$334
Select
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
$336
Select
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
$355
Select
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