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.
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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: Fri Sep 22 2017 Return: Sun Sep 24 2017 Trip spans 3 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
9h 32m
1 stop
Depart: Fri Sep 29 2017 Return: Sat Oct 7 2017 Trip spans 9 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
7h 26m
1 stop
Depart: Wed Oct 11 2017 Return: Wed Oct 18 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
7h 28m
1 stop
Depart: Fri Aug 25 2017 Return: Tue Aug 29 2017 Trip spans 5 days
Delta
Delta
MDW
HAV
16h 05m
1 stop
HAV
MDW
9h 27m
1 stop
Depart: Fri Dec 1 2017 Return: Mon Dec 4 2017 Trip spans 4 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
12h 33m
2 stops
Depart: Thu Aug 24 2017 Return: Thu Aug 31 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
17h 15m
2 stops
HAV
MDW
7h 32m
1 stop
Depart: Fri Nov 3 2017 Return: Wed Nov 8 2017 Trip spans 6 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
9h 18m
1 stop
Depart: Tue Jul 18 2017 Return: Tue Jul 25 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
15h 21m
2 stops
HAV
MDW
7h 31m
1 stop
Depart: Sat Dec 30 2017 Return: Tue Jan 9 2018 Trip spans 11 days
Delta
Delta
MDW
HAV
15h 21m
2 stops
HAV
MDW
11h 18m
2 stops
Depart: Fri Jul 7 2017 Return: Tue Jul 11 2017 Trip spans 5 days
Delta
Delta
MDW
NAS
14h 04m
1 stop
NAS
MDW
10h 26m
1 stop
Depart: Sat Jul 22 2017 Return: Sun Jul 30 2017 Trip spans 9 days
Delta
Delta
MDW
NAS
15h 47m
1 stop
NAS
MDW
10h 26m
1 stop
Depart: Thu Aug 3 2017 Return: Tue Aug 8 2017 Trip spans 6 days
Delta
Delta
MDW
NAS
13h 17m
1 stop
NAS
MDW
8h 07m
1 stop
Depart: Fri Aug 18 2017 Return: Fri Aug 25 2017 Trip spans 8 days
Delta
Delta
MDW
NAS
11h 54m
1 stop
NAS
MDW
11h 58m
1 stop
Depart: Wed Sep 20 2017 Return: Sun Sep 24 2017 Trip spans 5 days
Delta
Delta
MDW
NAS
4h 50m
1 stop
NAS
MDW
7h 07m
1 stop
Depart: Thu Sep 28 2017 Return: Sun Oct 1 2017 Trip spans 4 days
Delta
Delta
MDW
NAS
6h 52m
1 stop
NAS
MDW
5h 06m
1 stop
Depart: Wed Oct 4 2017 Return: Sun Oct 8 2017 Trip spans 5 days
Delta
Delta
MDW
NAS
11h 32m
1 stop
NAS
MDW
9h 18m
1 stop
Depart: Fri Oct 13 2017 Return: Mon Oct 16 2017 Trip spans 4 days
Delta
Delta
MDW
NAS
7h 32m
1 stop
NAS
MDW
8h 41m
1 stop
Depart: Fri Nov 3 2017 Return: Tue Nov 7 2017 Trip spans 5 days
Delta
Delta
MDW
NAS
4h 50m
1 stop
NAS
MDW
6h 02m
1 stop
Depart: Wed Dec 6 2017 Return: Wed Dec 13 2017 Trip spans 8 days
Delta
Delta
MDW
NAS
7h 32m
1 stop
NAS
MDW
6h 28m
1 stop
Depart: Thu Dec 7 2017 Return: Tue Dec 12 2017 Trip spans 6 days
Delta
Delta
MDW
NAS
8h 21m
1 stop
NAS
MDW
6h 28m
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
$328
Destination

Nassau
$447
Havana
$328
Airlines