Find Cheap 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: Mon May 8 2017 Return: Wed May 10 2017 Trip spans 3 days
Major Airline
Major Airline
ORD
HAV
22h 00m
1 stop
HAV
ORD
17h 45m
1 stop
Depart: Tue May 9 2017 Return: Wed May 17 2017 Trip spans 9 days
JetBlue
JetBlue
ORD
NAS
10h 40m
1 stop
NAS
ORD
11h 58m
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
11h 47m
1 stop
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: 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: Sat Apr 29 2017 Return: Wed May 3 2017 Trip spans 5 days
Delta
Delta
ORD
PUJ
8h 21m
1 stop
PUJ
ORD
9h 39m
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: Thu Jun 1 2017 Return: Mon Jun 5 2017 Trip spans 5 days
Copa Airlines
Copa Airlines
ORD
STI
23h 35m
1 stop
STI
ORD
22h 16m
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 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: Wed Oct 18 2017 Return: Wed Oct 25 2017 Trip spans 8 days
Avianca
Avianca
ORD
CUR
25h 07m
2 stops
CUR
ORD
20h 09m
2 stops
Depart: Wed Aug 30 2017 Return: Tue Sep 5 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 56m
1 stop
SJU
ORD
8h 16m
1 stop
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: 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: 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: Thu Oct 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
STT
9h 15m
1 stop
STT
ORD
8h 42m
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: Tue Jul 11 2017 Return: Tue Jul 18 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
NAS
9h 57m
1 stop
NAS
ORD
8h 44m
1 stop
Depart: Tue Oct 17 2017 Return: Tue Oct 31 2017 Trip spans 15 days
Spirit Airlines
Spirit Airlines
ORD
STT
9h 15m
1 stop
STT
ORD
8h 42m
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
$266
Destination

Nassau
$293
San Juan
$334
Saint Thomas Island
$338
Willemstad
$608
George Town
$460
Punta Cana
$330
Havana
$266
Santiago de los Caballeros
$434
Piarco
$351