Find Deals on 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 Mar 8 2017 Return: Thu Mar 23 2017 Trip spans 15 days
Spirit Airlines
Spirit Airlines
ORD
HAV
5h 27m
1 stop
HAV
ORD
11h 19m
1 stop
Depart: Mon Feb 27 2017 Return: Thu Mar 2 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
HAV
20h 05m
2 stops
HAV
ORD
11h 15m
2 stops
Depart: Mon Aug 21 2017 Return: Fri Sep 1 2017 Trip spans 12 days
Copa Airlines
Copa Airlines
ORD
HAV
21h 25m
1 stop
HAV
ORD
29h 22m
1 stop
Depart: Wed May 3 2017 Return: Tue May 9 2017 Trip spans 7 days
JetBlue
JetBlue
ORD
SJU
8h 30m
1 stop
SJU
ORD
8h 47m
1 stop
Depart: Mon Mar 6 2017 Return: Mon Mar 13 2017 Trip spans 7 days
American Airlines
American Airlines
ORD
PUJ
4h 21m
nonstop
PUJ
ORD
5h 18m
nonstop
Depart: Mon Mar 13 2017 Return: Wed Mar 15 2017 Trip spans 3 days
Delta
Delta
MDW
HAV
6h 25m
1 stop
HAV
MDW
6h 50m
1 stop
Depart: Mon Feb 27 2017 Return: Fri Mar 3 2017 Trip spans 5 days
United
United
ORD
PUJ
4h 30m
nonstop
PUJ
ORD
5h 10m
nonstop
Depart: Wed Apr 19 2017 Return: Wed Apr 26 2017 Trip spans 8 days
Frontier
Frontier
ORD
PUJ
4h 38m
nonstop
PUJ
ORD
5h 14m
nonstop
Depart: Sun Jul 16 2017 Return: Sun Jul 23 2017 Trip spans 8 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Wed Apr 12 2017 Return: Tue Apr 18 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
HAV
10h 06m
1 stop
HAV
ORD
11h 07m
1 stop
Depart: Tue May 2 2017 Return: Sat May 6 2017 Trip spans 5 days
Avianca
Avianca
ORD
CUR
25h 07m
2 stops
CUR
ORD
20h 09m
2 stops
Depart: Sat Apr 1 2017 Return: Sun Apr 9 2017 Trip spans 9 days
Aeromexico
Aeromexico
ORD
HAV
22h 50m
2 stops
HAV
ORD
22h 50m
2 stops
Depart: Tue May 2 2017 Return: Sat May 6 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
HAV
5h 32m
1 stop
HAV
ORD
12h 09m
1 stop
Depart: Sun Jul 9 2017 Return: Fri Jul 14 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
HAV
20h 00m
1 stop
HAV
ORD
17h 00m
1 stop
Depart: Mon Jun 12 2017 Return: Tue Jun 20 2017 Trip spans 9 days
Air Canada
Air Canada
ORD
POP
16h 40m
2 stops
POP
ORD
20h 04m
2 stops
Depart: Fri May 5 2017 Return: Wed May 10 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
HAV
5h 33m
1 stop
HAV
ORD
7h 29m
1 stop
Depart: Mon May 1 2017 Return: Thu May 4 2017 Trip spans 4 days
Delta
Delta
MDW
HAV
6h 35m
1 stop
HAV
MDW
6h 26m
1 stop
Depart: Tue Apr 18 2017 Return: Tue Apr 25 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SJU
24h 20m
1 stop
SJU
ORD
9h 49m
1 stop
Depart: Sat Jun 3 2017 Return: Thu Jun 8 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
HAV
7h 56m
1 stop
HAV
ORD
7h 27m
1 stop
Depart: Mon May 8 2017 Return: Wed May 10 2017 Trip spans 3 days
American Airlines
American Airlines
ORD
PUJ
17h 07m
1 stop
PUJ
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.

Airports
Origin

Chicago
only $246
only $322
Destination

San Juan
$296
San Felipe de Puerto Plata
$571
Willemstad
$505
George Town
$460
Punta Cana
$322
Havana
$246