Find Deals on Flights from Chicago O'Hare International 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 O'Hare International to Caribbean

(Round-trip)
Depart: Tue Mar 14 2017 Return: Wed Mar 15 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
HAV
10h 32m
1 stop
HAV
ORD
11h 19m
1 stop
Depart: Tue Apr 4 2017 Return: Tue Apr 25 2017 Trip spans 22 days
JetBlue
JetBlue
ORD
SJU
8h 27m
1 stop
SJU
ORD
9h 49m
1 stop
Depart: Thu Jul 6 2017 Return: Mon Jul 10 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
HAV
20h 00m
1 stop
HAV
ORD
16h 30m
1 stop
Depart: Tue Aug 1 2017 Return: Wed Aug 9 2017 Trip spans 9 days
Copa Airlines
Copa Airlines
ORD
HAV
15h 15m
1 stop
HAV
ORD
17h 00m
1 stop
Depart: Mon Mar 6 2017 Return: Fri Mar 10 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
PUJ
4h 21m
nonstop
PUJ
ORD
5h 21m
nonstop
Depart: Wed Mar 1 2017 Return: Sun Mar 5 2017 Trip spans 5 days
United
United
ORD
PUJ
4h 30m
nonstop
PUJ
ORD
5h 10m
nonstop
Depart: Wed Apr 12 2017 Return: Wed Apr 19 2017 Trip spans 8 days
Delta
Delta
ORD
HAV
6h 35m
1 stop
HAV
ORD
8h 40m
1 stop
Depart: Mon Apr 24 2017 Return: Wed May 3 2017 Trip spans 10 days
Frontier
Frontier
ORD
PUJ
4h 42m
nonstop
PUJ
ORD
5h 14m
nonstop
Depart: Sun Apr 16 2017 Return: Wed Apr 26 2017 Trip spans 11 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Mon Jun 5 2017 Return: Thu Jun 8 2017 Trip spans 4 days
Air Canada
Air Canada
ORD
POS
17h 40m
1 stop
POS
ORD
18h 18m
1 stop
Depart: Tue Apr 11 2017 Return: Tue Apr 18 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
HAV
5h 32m
1 stop
HAV
ORD
6h 27m
1 stop
Depart: Wed May 3 2017 Return: Wed May 10 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
HAV
10h 06m
1 stop
HAV
ORD
9h 06m
1 stop
Depart: Thu Mar 30 2017 Return: Tue Apr 4 2017 Trip spans 6 days
Avianca
Avianca
ORD
CUR
25h 07m
2 stops
CUR
ORD
20h 09m
2 stops
Depart: Mon Jul 24 2017 Return: Tue Aug 8 2017 Trip spans 16 days
Major Airline
Major Airline
ORD
HAV
6h 18m
1 stop
HAV
ORD
8h 27m
1 stop
Depart: Tue May 2 2017 Return: Tue May 9 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
SJU
8h 28m
1 stop
SJU
ORD
8h 47m
1 stop
Depart: Thu May 4 2017 Return: Tue May 9 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
HAV
7h 54m
1 stop
HAV
ORD
7h 29m
1 stop
Depart: Sun Jun 4 2017 Return: Thu Jun 8 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
HAV
5h 32m
1 stop
HAV
ORD
7h 27m
1 stop
Depart: Tue Apr 18 2017 Return: Tue Apr 25 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SJU
24h 20m
nonstop
SJU
ORD
9h 49m
nonstop
Depart: Thu Mar 30 2017 Return: Tue Apr 25 2017 Trip spans 27 days
JetBlue
JetBlue
ORD
SJU
8h 27m
1 stop
SJU
ORD
9h 49m
1 stop
Depart: Tue Aug 15 2017 Return: Wed Aug 23 2017 Trip spans 9 days
American Airlines
American Airlines
ORD
SJU
4h 55m
nonstop
SJU
ORD
5h 02m
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
$246
Destination

San Juan
$288
Willemstad
$554
George Town
$439
Punta Cana
$322
Havana
$246
Piarco
$443